可循环手性Mn（Ⅲ）salen催化剂催化烯烃不对称环氧化反应研究
|
摘要
Salen是一种常见的多齿配体,它的两个N,两个O原子处于同一平面内,可以与多种金属形成配合物,由于中心金属原子在垂直于salen配体平面的轴向存在空轨道,可以十分方便地与其他物质配位,所以金属salen配合物在催化领域有着广泛的应用。随着近些年手性化合物需求量的迅速增长,手性Mn(Ⅲ)salen配合物开始被用于手性催化领域,而且由于其高的反应活性和对映选择性,它成为了最重要的手性催化剂之一。然而由于均相的手性Mn(Ⅲ) salen催化剂不易于产物分离,不易回收。所以,近十年来,对于非均相手性Mn(Ⅲ) salen催化剂的研究成为催化界的热点,它可以用于催化烯烃的不对称环氧化、外消旋二级醇的氧化动力学拆分和硫醚的不对称氧化等反应。
首先,本文考察了载体孔径精细调变对于不对称结构的Mn(Ⅲ) salen非均相催化剂的催化性能的影响,将不对称结构的Mn(Ⅲ) salen配合物固载到一系列孔径精细调变的MCM-41和MCM-48上,采用红外光谱、固体紫外光谱、N2吸附脱附、X-射线衍射等手段对催化剂进行了表征,表明催化剂被成功固载且载体结构未发生变化。通过烯烃不对称环氧化反应,考察了3-巯丙基三甲氧基硅烷对催化剂性能的影响,并确定了最佳用量。在此基础上,本文研究了孔径的精细调变对于催化剂性能的影响,发现固载到孔径较大的介孔材料上的Mn(Ⅲ) salen非均相催化剂获得了较高的催化活性和对映选择性。
其次,本文考察了不对称结构的Mn(Ⅲ) salen均相和非均相催化剂在不同氧化体系下的催化性能,将不对称结构的Mn(Ⅲ) salen配合物固载到MCM-41、MCM-48和SBA-15上,通过各种表征证明了活性组分固载到了载体上,且载体原有结构得到了很好的保持。n-CPBA和NaCIO丙种氧化剂用于烯烃的不对称环氧化反应,当使用非均相Mn(Ⅲ) salen催化剂时,两种氧化剂在反应中获得的底物转化率有显著的差异,而在使用均相Mn(Ⅲ) salen催化剂时,两种氧化剂获得的转化率基本一致,换句话说,Mn(Ⅲ) salen配合物的非均相化对于m-CPBA和NaClO有不同的影响。为了研究这一现象,文中采用紫外-可见光谱及反应动力学研究了两个反应体系,发现由于NaClO是一种温和的氧化剂,在反应过程中无明显的催化剂中间体[salen-Mn(V)=O]+累积失活的现象,这是NaClO在非均相条件下取得较好的转化率的原因。此外,与以MCM-41为载体的非均相Mn(Ⅲ) salen催化剂相比,固载到MCM-48和SBA-15上的非均相催化剂获得了较好的催化活性和对映选择性,这与MCM-48拥有三维孔道结构及SBA-15拥有大的孔径有利于底物分子扩散有关。
再次,本文采用废轮胎热解炭黑作为载体,不加入任何有机硅烷,没有采用氧化方式改变炭黑表面含氧基团的数量,十分经济的将手性Mn(Ⅲ) salen配合物直接共价固载到了炭黑表面,制备的非均相Mn(Ⅲ) salen催化剂在烯烃不对称环氧化反应中取得了很好的催化结果,特别是在1-苯基环己烯的不对称环氧化反应中,获得了高于均相催化剂的ee值。此外,该类非均相催化剂可以循环使用三次。
最后,本文分别利用1,2-乙硫醇、1,3-丙二硫醇和1,6-己二硫醇与Mn(Ⅲ)salen配合物构建了一系列环状硫醚手性Mn(Ⅲ) salen配合物。通过核磁共振、质谱和红外光谱表明环状硫醚结构的成功合成。该类催化剂在反应体系中保持了很高的催化活性,在加入正己烷的情况下,极容易从反应体系中分离出来。本文确定了最佳的反应体系,即NaCIO与PPNO的氧化体系,采用的最佳溶剂为二氯甲烷。在烯烃的不对称环氧化反应中,取得了与环状硫醚手性Mn(Ⅲ)salen配合物结构相似的Mn(Ⅲ) salen配合物可比的催化性能,而且该类催化剂可以循环使用六次。
Salen is a common chelating ligand, in which two N atoms and O atoms were on the same plane, and it can coordinate with many kinds of transit metal. As a result of the existence of unoccupied orbital in metal salen complexes axially, which can coordinate with many functionalized groups, metal salen complexes are widely applied in catalysis field. With the increased demand of chiral compounds, enantioselective metal salen complexes are used in chiral catalysis area, and because of their high activity and enatioselectivity, they have become privileged chiral catalysts. Among metal salen complexes, Mn(Ⅲ) salen complex proves to be an important complex, which can catalyzed many reactions, such asymmetric epoxidation of olefins, oxidation kinetics resolution of racemic secondary alcohols and asymmetric oxidation of sulfide. However, due to the difficulty in product separation and catalyst recycling for homogeneous Mn(Ⅲ) salen complex, heterogeneous Mn(Ⅲ) salen catalysts have attracted much attention in last decade.
First, it was investigated that the effect of fine tuning pore size for the catalytic performance of unsymmetric Mn(Ⅲ) salen heterogeneous catalysts, and an unsymmetric Mn(Ⅲ) salen complex was immobilized on a series of MCM-41and MCM-48with fine-tuning pore size. These heterogeneous catalysts were characterized by FT-IR, DR UV-vis, N2sorption and XRD, and these characterizations indicated that the active specie was grafted successfully and the structures of supports were kept well. The dosage of3-Mercaptopropyltrimethoxysilane was studied in epoxidation of olefins, which could influence the catalytic performance of heterogeneous catalysts. The optimum organosilane was determined, and on the basis of this, the effect of fine-tuning pore size for catalytic performance of catalysts was investigated. It was found that the heterogeneous catalysts immobilized on mesoporous silica with larger pore size showed higher catalytic activity and enantioselectivity.
Second, it was studied that the comparison of catalytic performace of homogeneous and heterogeneous Mn(Ⅲ) salen catalysts using different oxidants, and two kinds of unsymmetric Mn(Ⅲ) salen complexes were grafted on mesoporous silica MCM-41, MCM-48and SBA-15. Several characterizations were employed and they indicated that Mn(Ⅲ) salen complexes were immobilized on the support successfully and the mesoporous structures of supports were retained very well. Two oxidants, m-CPBA and NaCIO, were applied in asymmetric epoxidation of unfunctionalized olefins. As the heterogeneous catalysts Mn(Ⅲ) salen catalysts were chosen, the conversions obtained by two oxidants showed remarkable different (NaCIO obtained great higher conversions), while the conversions obtained by two oxidants presented no obvious difference using homogeneous catalysts. In other words, the heterogenization of Mn(Ⅲ) salen complexes gave different influence for two oxidation system of m-CPBA and NaCIO. In order to research this phenomenon, UV-vis spectra and reaction kinetics were employed to study two oxidation system mentioned above, and it was found that as a result of the mildness of NaClO, no obvious accumulation of intermediate [Mn(Ⅴ)=O salen]+was observed. This was the reason that NaClO gave higher conversions in heterogeneous condition. In addition, compared with the heterogeneous catalysts immobilized MCM-41, the heterogeneous catalysts immobilized on MCM-48and SBA-15showed better catalytic activity and enantioselectivity, and this was due to3D pore structure of MCM-48and larger pore size of SBA-15, which improved molecular diffusion.
Third, in this paper, pyrolytic waste tire char (PWTC) was chosen as support, and without any organosilane and oxidation process, Mn(Ⅲ) salen complexes were immobilized on PWTC directly. The prepared heterogeneous Mn(Ⅲ) salen catalysts obtained good catalytic results in asymmetric epoxidation of olefins, and especially in the epoxidation of1-phenylcyclohexene, they obtained higher ee values than their homogeneous counterparts. Moreover, the heterogeneous catalyst could be recycled three times.
Fourth, with the employment of1,2-ethanedithiol,1,3-propanedithiol and1,6-hexanedithiol, a series of cyclic sulfide Mn(Ⅲ) salen complexes were synthesized. Though the characterizations of NMR, MS and FT-IR, it was confirmed that the cyclic sulfide structure was synthesized successfully. In asymmetric epoxidation of olefins, the oxidation system of NaClO/PPNO was chosen, and dichloromethane was employed as solvent. These cyclic sulfide Mn(Ⅲ) salen complexes presented good catalytic performance in asymmetric epoxidation of unfunctionalized olefins. With the addition of hexane, these Mn(Ⅲ) salen complexes were separated easily and they could be recycled six times.
首先,本文考察了载体孔径精细调变对于不对称结构的Mn(Ⅲ) salen非均相催化剂的催化性能的影响,将不对称结构的Mn(Ⅲ) salen配合物固载到一系列孔径精细调变的MCM-41和MCM-48上,采用红外光谱、固体紫外光谱、N2吸附脱附、X-射线衍射等手段对催化剂进行了表征,表明催化剂被成功固载且载体结构未发生变化。通过烯烃不对称环氧化反应,考察了3-巯丙基三甲氧基硅烷对催化剂性能的影响,并确定了最佳用量。在此基础上,本文研究了孔径的精细调变对于催化剂性能的影响,发现固载到孔径较大的介孔材料上的Mn(Ⅲ) salen非均相催化剂获得了较高的催化活性和对映选择性。
其次,本文考察了不对称结构的Mn(Ⅲ) salen均相和非均相催化剂在不同氧化体系下的催化性能,将不对称结构的Mn(Ⅲ) salen配合物固载到MCM-41、MCM-48和SBA-15上,通过各种表征证明了活性组分固载到了载体上,且载体原有结构得到了很好的保持。n-CPBA和NaCIO丙种氧化剂用于烯烃的不对称环氧化反应,当使用非均相Mn(Ⅲ) salen催化剂时,两种氧化剂在反应中获得的底物转化率有显著的差异,而在使用均相Mn(Ⅲ) salen催化剂时,两种氧化剂获得的转化率基本一致,换句话说,Mn(Ⅲ) salen配合物的非均相化对于m-CPBA和NaClO有不同的影响。为了研究这一现象,文中采用紫外-可见光谱及反应动力学研究了两个反应体系,发现由于NaClO是一种温和的氧化剂,在反应过程中无明显的催化剂中间体[salen-Mn(V)=O]+累积失活的现象,这是NaClO在非均相条件下取得较好的转化率的原因。此外,与以MCM-41为载体的非均相Mn(Ⅲ) salen催化剂相比,固载到MCM-48和SBA-15上的非均相催化剂获得了较好的催化活性和对映选择性,这与MCM-48拥有三维孔道结构及SBA-15拥有大的孔径有利于底物分子扩散有关。
再次,本文采用废轮胎热解炭黑作为载体,不加入任何有机硅烷,没有采用氧化方式改变炭黑表面含氧基团的数量,十分经济的将手性Mn(Ⅲ) salen配合物直接共价固载到了炭黑表面,制备的非均相Mn(Ⅲ) salen催化剂在烯烃不对称环氧化反应中取得了很好的催化结果,特别是在1-苯基环己烯的不对称环氧化反应中,获得了高于均相催化剂的ee值。此外,该类非均相催化剂可以循环使用三次。
最后,本文分别利用1,2-乙硫醇、1,3-丙二硫醇和1,6-己二硫醇与Mn(Ⅲ)salen配合物构建了一系列环状硫醚手性Mn(Ⅲ) salen配合物。通过核磁共振、质谱和红外光谱表明环状硫醚结构的成功合成。该类催化剂在反应体系中保持了很高的催化活性,在加入正己烷的情况下,极容易从反应体系中分离出来。本文确定了最佳的反应体系,即NaCIO与PPNO的氧化体系,采用的最佳溶剂为二氯甲烷。在烯烃的不对称环氧化反应中,取得了与环状硫醚手性Mn(Ⅲ)salen配合物结构相似的Mn(Ⅲ) salen配合物可比的催化性能,而且该类催化剂可以循环使用六次。
Salen is a common chelating ligand, in which two N atoms and O atoms were on the same plane, and it can coordinate with many kinds of transit metal. As a result of the existence of unoccupied orbital in metal salen complexes axially, which can coordinate with many functionalized groups, metal salen complexes are widely applied in catalysis field. With the increased demand of chiral compounds, enantioselective metal salen complexes are used in chiral catalysis area, and because of their high activity and enatioselectivity, they have become privileged chiral catalysts. Among metal salen complexes, Mn(Ⅲ) salen complex proves to be an important complex, which can catalyzed many reactions, such asymmetric epoxidation of olefins, oxidation kinetics resolution of racemic secondary alcohols and asymmetric oxidation of sulfide. However, due to the difficulty in product separation and catalyst recycling for homogeneous Mn(Ⅲ) salen complex, heterogeneous Mn(Ⅲ) salen catalysts have attracted much attention in last decade.
First, it was investigated that the effect of fine tuning pore size for the catalytic performance of unsymmetric Mn(Ⅲ) salen heterogeneous catalysts, and an unsymmetric Mn(Ⅲ) salen complex was immobilized on a series of MCM-41and MCM-48with fine-tuning pore size. These heterogeneous catalysts were characterized by FT-IR, DR UV-vis, N2sorption and XRD, and these characterizations indicated that the active specie was grafted successfully and the structures of supports were kept well. The dosage of3-Mercaptopropyltrimethoxysilane was studied in epoxidation of olefins, which could influence the catalytic performance of heterogeneous catalysts. The optimum organosilane was determined, and on the basis of this, the effect of fine-tuning pore size for catalytic performance of catalysts was investigated. It was found that the heterogeneous catalysts immobilized on mesoporous silica with larger pore size showed higher catalytic activity and enantioselectivity.
Second, it was studied that the comparison of catalytic performace of homogeneous and heterogeneous Mn(Ⅲ) salen catalysts using different oxidants, and two kinds of unsymmetric Mn(Ⅲ) salen complexes were grafted on mesoporous silica MCM-41, MCM-48and SBA-15. Several characterizations were employed and they indicated that Mn(Ⅲ) salen complexes were immobilized on the support successfully and the mesoporous structures of supports were retained very well. Two oxidants, m-CPBA and NaCIO, were applied in asymmetric epoxidation of unfunctionalized olefins. As the heterogeneous catalysts Mn(Ⅲ) salen catalysts were chosen, the conversions obtained by two oxidants showed remarkable different (NaCIO obtained great higher conversions), while the conversions obtained by two oxidants presented no obvious difference using homogeneous catalysts. In other words, the heterogenization of Mn(Ⅲ) salen complexes gave different influence for two oxidation system of m-CPBA and NaCIO. In order to research this phenomenon, UV-vis spectra and reaction kinetics were employed to study two oxidation system mentioned above, and it was found that as a result of the mildness of NaClO, no obvious accumulation of intermediate [Mn(Ⅴ)=O salen]+was observed. This was the reason that NaClO gave higher conversions in heterogeneous condition. In addition, compared with the heterogeneous catalysts immobilized MCM-41, the heterogeneous catalysts immobilized on MCM-48and SBA-15showed better catalytic activity and enantioselectivity, and this was due to3D pore structure of MCM-48and larger pore size of SBA-15, which improved molecular diffusion.
Third, in this paper, pyrolytic waste tire char (PWTC) was chosen as support, and without any organosilane and oxidation process, Mn(Ⅲ) salen complexes were immobilized on PWTC directly. The prepared heterogeneous Mn(Ⅲ) salen catalysts obtained good catalytic results in asymmetric epoxidation of olefins, and especially in the epoxidation of1-phenylcyclohexene, they obtained higher ee values than their homogeneous counterparts. Moreover, the heterogeneous catalyst could be recycled three times.
Fourth, with the employment of1,2-ethanedithiol,1,3-propanedithiol and1,6-hexanedithiol, a series of cyclic sulfide Mn(Ⅲ) salen complexes were synthesized. Though the characterizations of NMR, MS and FT-IR, it was confirmed that the cyclic sulfide structure was synthesized successfully. In asymmetric epoxidation of olefins, the oxidation system of NaClO/PPNO was chosen, and dichloromethane was employed as solvent. These cyclic sulfide Mn(Ⅲ) salen complexes presented good catalytic performance in asymmetric epoxidation of unfunctionalized olefins. With the addition of hexane, these Mn(Ⅲ) salen complexes were separated easily and they could be recycled six times.
引文
[1]Schiff H. Synthesis of Sciiff Bases. Ann. Suppl,1864,3(1):343
[2]Yamada S. Recent aspects of the stereochemistry of schiff-base-metal complexes. Coord Chem Rev,1966,1(4):415-437
[3]Atwood D A, Harvey M J. Group 13 Compounds Incorporating Salen Ligands. Chem Rev, 2000,101(1):37-52
[4]Dzugan S J, Goedken V L. Factors affecting aluminum-carbon bond reactivity of tetradentate Schiff-base organoaluminum complexes. Inorg Chem,1986,25(16):2858-2864
[5]Atwood D A, Hill M S, Jegier J A, et al. The Use of Five-Coordinate Aluminum Alkyls To Prepare Molecules Containing a Single Al-O-Si Linkage. Organometallics,1997,16(12): 2659-2664
[6]Carbonaro L, Isola M, La Pegna P, et al. Spectrophotometric Study of the Equilibria between Nickel(Ⅱ) Schiff-Base Complexes and Alkaline Earth or Nickel(II) Cations in Acetonitrile Solution. Inorg Chem,1999,38(24):5519-5525
[7]Sanchez M, Harvey M J, Nordstrom F, et al. Salen-Type Compounds of Calcium and Strontium. Inorg Chem,2002,41(21):5397-5402
[8]Haak R M, Decortes A, Escudero-Adan E C, et al. Shape-Persistent Octanuclear Zinc Salen Clusters:Synthesis, Characterization, and Catalysis. Inorg Chem,2011,50(17):7934-7936
[9]Feng W, Zhang Y, Zhang Z, et al. Anion-Induced Self-Assembly of Luminescent and Magnetic Homoleptic Cyclic Tetranuclear Ln4(Salen)4 and Ln4(Salen)2 Complexes (Ln= Nd, Yb, Er, or Gd). Inorg Chem,2012,51(21):11377-11386
[10]Thurston J H, Tang C G Z, Trahan D W, et al. Toward Rational Control of Metal Stoichiometry in Heterobimetallic Coordination Complexes:Synthesis and Characterization of Pb(Hsal)2(Cu(salen*))2, [Pb(NO3)(Cu(salen*))2](NO3), Pb(OAc)2(Cu(salen*)), and [Pb(OAc)(Ni(salen*))2](OAc). Inorg Chem,2004,43(8):2708-2713
[11]Wei P, Atwood D A. Bimetallic Borate Derivatives of the Salen Ligands. Inorg Chem,1997, 36(18):4060-4065
[12]El-Behery M, El-Twigry H. Synthesis, magnetic, spectral, and antimicrobial studies of Cu(Ⅱ), Ni(Ⅱ) Co(Ⅱ), Fe(Ⅲ), and UO2(Ⅱ) complexes of a new Schiff base hydrazone derived from 7-chloro-4-hydrazinoquinoline. Spectrochim Acta, Part A,2007,66(1):28-36
[13]Li T-R, Yang Z-Y, Wang B-D. Synthesis, Characterization and Antioxidant Activity of Naringenin Schiff Base and Its Cu(II), Ni(II), Zn(II) Complexes. Chem Pharm Bull,2007,55(1): 26-28
[14]Pandya N, Khan N-u H, Prathap K J, et al. DNA Binding, Antioxidant Activity, and DNA Damage Protection of Chiral Macrocyclic Mn(Ⅲ) Salen Complexes. Chirality,2012,24(12): 1063-1073
[15]Reddy P R, Shilpa A. Synthesis, Characterization, and DNA-Binding and-Cleavage Properties of Dinuclear Cu-II-Salophen/Salen Complexes. Chem Biodivers,2011,8(7): 1245-1265
[16]Khan N-u H, Pandya N, Kumar M, et al. Influence of chirality using Mn(iii) salen complexes on DNA binding and antioxidant activity. Org Biomol Chem,2010,8(19):4297-4307
[17]Peng B, Zhou W H, Yan L, et al. DNA-binding and cleavage studies of chiral Mn(III) salen complexes. Transition Met Chem,2009,34(2):231-237
[18]Khan N U H, Pandya N, Kureshy R I, et al. Synthesis, characterization, DNA binding and cleavage studies of chiral Ru(II) salen complexes. Spectrochim. Acta, Part A,2009,74(1): 113-119
[19]Ansari K I, Grant J D, Woldemariam G A, et al. Iron(III)-salen complexes with less DNA cleavage activity exhibit more efficient apoptosis in MCF7 cells. Org Biomol Chem,2009,7(5): 926-932
[20]Clever G H, Soltl Y, Burks H, et al. Metal-salen-base-pair complexes inside DNA: Complexation overrides sequence information. Chem Eur J,2006,12(34):8708-8718
[21]Verquin G, Fontaine G, Bria M, et al. DNA modification by oxovanadium(IV) complexes of salen derivatives. J Biol Inorg Chem,2004,9(3):345-353
[22]Brown R S, Nielsen M, Gothelf K V. Self-assembly of aluminium-salen coupled nanostructures from encoded modules with cleavable disulfide DNA-linkers. Chem Commun, 2004, (13):1464-1465
[23]Zhou X, Shearer J, Rokita S E. A Ni(salen)-biotin conjugate for rapid isolation of accessible DNA. J Am Chem Soc,2000,122(37):9046-9047
[24]Cheng C C, Lu Y L. Novel water-soluble 4,4-disubstituted ruthenium(III)-salen complexes in DNA stranded scission. J Chin Chem Soc,1998,45(5):611-617
[25]Routier S, Bernier J L, Waring M J, et al. Synthesis of a functionalized salen copper complex and its interaction with DNA. J Org Chem,1996,61(7):2326-2331
[26]Srinivasan K, Michaud P, Kochi J K. Epoxidation of olefins with cationic (salen)MnⅢ complexes-the modulation of catalytic activity by substituents. J Am Chem Soc,1986,108(9): 2309-2320
[27]Rihter B, Masnovi J. Oxidation of alkynes and ylides by oxo(salen)chromium(V) (salen=N,N'-ethylenebis-salicylideneiminato) trifluoromethanesulphonate. J Chem Soc, Chem Commun,1988, (1):35-37
[28]Finashina E D, Kramareva N V, Kustov L M. Oxidation of catecholamines on chitosan-immobilized Co(Ⅱ) salen complexes. Macromol Symp,2003,204(1):205-217
[29]Kervinen K, Kopi H, Leskela M, et al. Oxidation of veratryl alcohol by molecular oxygen in aqueous solution catalyzed by cobalt salen-type complexes:the effect of reaction conditions. J Mol Catal A:Chem,2003,203(1-2):9-19
[30]Milo A, Neumann R. An achiral manganese salen catalyst encapsulated in a peptidic phosphonate homochiral solid for the enantioselective formation of diols by consecutive epoxidation and hydration reactions. Chem Commun,2011,47(9):2535-2537
[31]Li B, Bai S, Wang X, et al. Hydration of Epoxides on [CoⅢ(salen)] Encapsulated in Silica-Based Nanoreactors. Angew Chem Int Ed,2012,51(46):11517-11521
[32]Paddock R L, Nguyen S T. Chemical CO2 Fixation:Cr(Ⅲ) Salen Complexes as Highly Efficient Catalysts for the Coupling of CO2 and Epoxides. J Am Chem Soc,2001,123(46): 11498-11499
[33]Darensbourg D J, Billodeaux D R. Aluminum Salen Complexes and Tetrabutylammonium Salts:A Binary Catalytic System for Production of Polycarbonates from CO2 and Cyclohexene Oxide. Inorg Chem,2005,44(5):1433-1442
[34]Alvaro M, Baleizao C, Carbonell E, et al. Polymer-bound aluminium salen complex as reusable catalysts for CO2 insertion into epoxides. Tetrahedron,2005,61(51):12131-12139
[35]We R, Noda K, Ito Y, et al. Enantioselective epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes. Tetrahedron Lett,1991,32(8):1055-1058
[36]Zhang W, Loebach J L, Wilson S R, et al. Enantioselective epoxidation of unfunctionalized olefins catalyzed by salen manganese complexes. J Am Chem Soc,1990,112(7):2801-2803
[37]Palucki M, Hanson P, Jacobsen E N. Asymmetric oxidation of sulfides with H2O2 catalyzed by (salen)Mn(III) complexes. Tetrahedron Lett,1992,33(47):7111-7114
[38]Sun W, Wang H W, Xia C Q et al. Chiral-Mn(salen)-complex-catalyzed kinetic resolution of secondary alcohols in water. Angew Chem Inter Ed,2003,42(9):1042-+
[39]Tokunaga M, Larrow J F, Kakiuchi F, et al. Asymmetric Catalysis with Water:Efficient Kinetic Resolution of Terminal Epoxides by Means of Catalytic Hydrolysis. Science,1997, 277(5328):936-938
[40]Bartoli G, Bosco M, Carlone A, et al. Asymmetric Catalytic Synthesis of Enantiopure N-Protected 1,2-Amino Alcohols. Org Lett,2004,6(22):3973-3975
[41]Bartoli G, Bosco M, Carlone A, et al. Asymmetric Aminolysis of Aromatic Epoxides:A Facile Catalytic Enantioselective Synthesis of anti-β-Amino Alcohols. Org Lett,2004,6(13): 2173-2176
[42]Loy R N, Jacobsen E N. Enantioselective Intramolecular Openings of Oxetanes Catalyzed by (salen)Co(III) Complexes:Access to Enantioenriched Tetrahydrofurans. J Am Chem Soc, 2009,131(8):2786-2787
[43]Belokon Y N, Green B, Ikonnikov N S, et al. The asymmetric addition of trimethylsilyl cyanide to ketones catalysed by a bimetallic, chiral (salen)titanium complex. Tetrahedron Lett, 1999,40(46):8147-8150
[44]Kim S S, Lee S H, Kwak J M. Enantioselective cyanosilylation of ketones catalyzed by Mn(salen)/Ph3PO. Tetrahedron:Asymmetry,2006,17(8):1165-1169
[45]Kim S S, Kwak J M. Asymmetric addition of trimethylsilyl cyanide to ketones catalyzed by Al(salen)/triphenylphosphine oxide. Tetrahedron,2006,62(1):49-53
[46]Cozzi P G, Papa A, Umani-Ronchi A. Enantioselective addition of Et2Zn to aldehydes promoted by a chiral Schiff base metal complex. Tetrahedron Lett,1996,37(26):4613-4616
[47]Cozzi P G Enantioselective Alkynylation of Ketones Catalyzed by Zn(Salen) Complexes. Angew Chem Int Ed,2003,42(25):2895-2898
[48]Park J, Lang K, Abboud K A, et al. Self-Assembled Dinuclear Cobalt(II)-Salen Catalyst Through Hydrogen-Bonding and Its Application to Enantioselective Nitro-Aldol (Henry) Reaction. J Am Chem Soc,2008,130(49):16484-16485
[49]Kogami Y, Nakajima T, Ashizawa T, et al. Enantioselective Henry Reaction Catalyzed by Optically Active Ketoiminatocobalt Complexes. Chem Lett,2004,33(5):614-615
[50]Frunza L, Kosslick H, Landmesser H, et al. Host/guest interactions in nanoporous materials I. The embedding of chiral salen manganese(III) complex into mesoporous silicates. J Mol Catal A:Chem,1997,123(2-3):179-187
[51]Piaggio P, McMorn P, Langham C, et al. Asymmetric epoxidation of stilbene by manganese(III) chiral salen complex immobilized in Al-MCM-41. New J Chem,1998,22(11): 1167-1169
[52]Kim G J, Kim S H. Immobilization of new Mn(salen) complex over MCM-41 and its activity in asymmetric epoxidation of styrene. Catal Lett,1999,57(3):139-143
[53]Piaggio P, Langham C, McMorn P, et al. Catalytic asymmetric epoxidation of stilbene using a chiral salen complex immobilized in Mn-exchanged Al-MCM-41. J Chem Soc, Perkin Trans 2, 2000, (1):143-148
[54]Kureshy R I, Khan N U H, Abdi S H R, et al. Dicationic chiral Mn(Ⅲ) salen complex exchanged in the interlayers of montmorillonite clay:a heterogeneous enantioselective catalyst for epoxidation of nonfunctionalized alkenes. J Catal,2004,221(1):234-240
[55]Das P, Kuzniarska-Biernacka I, Silva A R, et al. Encapsulation of chiral Mn(Ⅲ) salen complexes into aluminium pillared clays:Application as heterogeneous catalysts in the epoxidation of styrene. J Mol Catal A:Chem,2006,248(1-2):135-143
[56]Piaggio P, McMorn P, Murphy D, et al. Enantioselective epoxidation of (Z)-stilbene using a chiral Mn(Ⅲ)-salen complex:effect of immobilisation on MCM-41 on product selectivity. J Chem Soc, Perkin Trans 2,2000, (10):2008-2015
[57]Zhou X-G. Yu X-Q, Huang J-S, et al. Asymmetric epoxidation of alkenes catalysed by chromium binaphthyl Schiff base complex supported on MCM-41. Chem Commun,1999,0(18): 1789-1790
[58]Xiang S, Zhang Y L, Xin Q, et al. Enantioselective epoxidation of olefins catalyzed by Mn (salen)/MCM-41 synthesized with a new anchoring method. Chem Commun,2002, (22): 2696-2697
[59]Zhang H D, Xiang S, Li C. Enantioselective epoxidation of unfunctionalised olefins catalyzed by Mn(salen) complexes immobilized in porous materials via phenyl sulfonic group. Chem Commun,2005, (9):1209-1211
[60]Zhang H D, Xiang S, Xiao J L, et al. Heterogeneous enantioselective epoxidation catalyzed by Mn(salen) complexes grafted onto mesoporous materials by phenoxy group. J Mol Catal A: Chem,2005,238(1-2):175-184
[61]Zhang H D, Zhang Y M, Li C. Asymmetric epoxidation of unfunctionalized olefins catalyzed by Mn(salen) axially immobilized onto insoluble polymers. Tetrahedron:Asymmetry, 2005,16(14):2417-2423
[62]Shen H S, Fu X K, Bao H B, et al. Synthesis and characterization of a new kind of immobilized Mn(salen) and catalytic epoxidation of styrene on the catalyst. Polym Adv Technol, 2009,20(2):77-83
[63]Bai R F, Fu X K, Bao H B, et al. Chiral Salen Mn(III) complex axial coordination immobilized on diamine modified ZSPP and their catalytic epoxidation of styrene. Catal Commun,2008,9(7):1588-1594
[64]Huang J, Fu X K, Miao Q. Synthesis of a novel type of chiral salen Mn(III) complex immobilized on crystalline zinc poly(styrene-phenylvinylphosphonate)-phosphate (ZnPS-PVPP) as effective catalysts for asymmetric epoxidation of unfunctionalized olefins. Catal Sci Technol, 2011,1(8):1472-1482
[65]Huang J, Fu X K, Miao Q. Catalytic asymmetric epoxidation of unfunctionalized olefins using a series novel type of layered crystalline organic polymer-inorganic hybrid zinc phosphonate-phosphate immobilized aryldiamine modified chiral salen Mn(Ⅲ) complex. Appl Catal A:Gen,2011,407(1-2):163-172
[66]Hu X Y, Fu X K, Xu J W, et al. A novel layered organic polymer-inorganic hybrid zinc poly (styrene-phenylvinylphosphonate)-phosphate immobilized chiral salen Mn(Ⅲ) catalyst large-scale asymmetric epoxidation of unfunctionalized olefins. J Organomet Chem,2011, 696(15-16):2797-2804
[67]Liu Z J, Fu X K, Hu X Y, et al. Asymmetric epoxidation of unfunctionalized olefins catalyzed by chiral salen Mn(III) immobilized onto sulfoalkyl modified zirconium poly(styrene-isopropenyl phosphonate)-phosphate and zirconium poly(styrene-phenylvivyl phosphonate)-phosphate. J Organomet Chem,2012,713(1):157-162
[68]Huang J, Fu X K, Wang G, et al. A high efficient large-scale asymmetric epoxidation of unfunctionalized olefins employing a novel type of chiral salen Mn(III) immobilized onto layered crystalline aryldiamine modified zinc poly(styrene-phenylvinylphosphonate)-phosphate. J Mol Catal A:Chem,2012,357:162-173
[69]Luo Y F, Fu X K, Zou X C, et al. Effect of Axial Linker Group on Heterogeneous Chiral Salen Mn(III) Catalyzed Enantioselective Epoxidation of Unfunctionalized Olefins. Chin J Inorg Chem,2011,27(7):1302-1308
[70]Huang J, Fu X K, Wang C W, et al. Chiral salen Mn(Ⅲ) immobilized onto sulfoalkyl-modified zinc poly(styrene-phenylvinylphosphonate)-phosphate as effective catalysts for epoxidation of unfunctionalized olefins. Microporous Mesoporous Mater,2012,153(1): 294-301
[71]Jia Z Y, Fu X K, Luo Y F, et al. Chiral Salen Mn(Ⅲ) Complex Axial Coordination Immobilized on Diamine Modified Alspp and Highly Efficient Large-Scale Epoxidation of Olefins as a Recoverable Catalyst. J Inorg Organomet Polym Mater,2012,22(2):415-422
[72]Kim Y S, Guo X F, Kim G J. Highly active new chiral Co(Ⅲ) salen catalysts immobilized by electrostatic interaction with sulfonic acid linkages on ordered mesoporous SBA-16 silica. Chem Commun,2009, (28):4296-4298
[73]Gong B W, Fu X K, Chen J X, et al. Synthesis of a new type of immobilized chiral salen Mn(III) complex as effective catalysts for asymmetric epoxidation of unfunctionalized olefins. J Catal,2009,262(1):9-17
[74]Silva A R, Freire C, de Castro B. Jacobsen catalyst anchored onto an activated carbon as an enantioselective heterogeneous catalyst for the epoxidation of alkenes. Carbon,2004,42(14): 3027-3030
[75]Silva A R, Budarin V, Clark J H, et al. Chiral manganese(Ⅲ) Schiff base complexes anchored onto activated carbon as enantioselective heterogeneous catalysts for alkene epoxidation. Carbon,2005,43(10):2096-2105
[76]Tu X B, Fu X K, Hu X Y, et al. Chiral salen Mn(Ⅲ) immobilized on sulfoalkyl modified ZSP-IPPA as an effective catalyst for asymmetric epoxidation of unfunctionalized olefins. Inorg Chem Commun,2010,13(3):404-407
[77]Kim G J, Shin J H. The catalytic activity of new chiral salen complexes immobilized on MCM-41 by multi-step grafting in the asymmetric epoxidation. Tetrahedron Lett,1999,40(37): 6827-6830
[78]Kim G J, Park D W. The catalytic activity of new chiral salen complexes immobilized on MCM-41 in the asymmetric hydrolysis of epoxides to diols. Catal Today,2000,63(2-4):537-547
[79]Zhao D, Zhao J, Zhao S, et al. Preparation of MCM-41 supported heterogenized chiral Salen Mn (Ⅲ) complex and the catalytic activity in the asymmetric epoxidation. J Inorg Organomet Polym Mater,2007,17(4):653-659
[80]Dhahagani K, Rajesh J, Kannan R, et al. Asymmetric Henry reaction of aldehydes catalyzed by recyclable an MCM-41 supported copper(II) salen complex. Tetrahedron:Asymmetry,2011, 22(8):857-865
[81]Kureshy R I, Ahmad I, Khan N H, et al. Encapsulation of a chiral Mn-III(salen) complex in ordered mesoporous silicas:an approach towards heterogenizing asymmetric epoxidation catalysts for non-functionalized alkenes. Tetrahedron:Asymmetry,2005,16(21):3562-3569
[82]Kureshy R I, Ahmad I, Khan N H, et al. Chiral Mn(III) salen complexes covalently bonded on modified MCM-41 and SBA-15 as efficient catalysts for enantioselective epoxidation of nonfunctionalized alkenes. J Catal,2006,238(1):134-141
[83]Yu K, Gu Z, Ji R, et al. Effect of pore size on the performance of mesoporous material supported chiral Mn(III) salen complex for the epoxidation of unfunctionalized olefins. J Catal, 2007,252(2):312-320
[84]Bigi F, Moroni L, Maggi R, et al. Heterogeneous enantioselective epoxidation of olefins catalysed by unsymmetrical (salen) Mn(Ⅲ) complexes supported on amorphous or MCM-41 silica through a new triazine-based linker. Chem Commun,2002, (7):716-717
[85]Kuzniarska-Biernacka I, Silva A R, Carvalho A P, et al. Organo-laponites as novel mesoporous supports for manganese(Ⅲ) salen catalysts. Langmuir,2005,21(23):10825-10834
[86]Silva A R, Budarin V, Clark J H, et al. Organo-functionalized activated carbons as supports for the coyalent attachment of a chiral manganese(Ⅲ) salen complex. Carbon,2007,45(10): 1951-1964
[87]Roy T, Kureshy R I, Khan N, et al. Immobilized dimeric chiral Mn(Ⅲ) salen complex on short channel ordered mesoporous silica as an effective catalyst for the epoxidation of non-functionalized alkenes. Tetrahedron,2012,68(31):6314-6322
[88]Song C E, Roh E J, Yu B M, et al. Heterogeneous asymmetric epoxidation of alkenes catalysed by a polymer-bound (pyrrolidine salen)manganese(Ⅲ) complex. Chem Commun,2000, (7):615-616
[89]Silva A R, Wilson K, Clark J H, et al. Covalent attachment of chiral manganese(Ⅲ) salen complexes onto functionalised hexagonal mesoporous silica and application to the asymmetric epoxidation of alkenes. Microporous Mesoporous Mater,2006,91(1-3):128-138
[90]Minutolo F, Pini D, Petri A, et al. Heterogeneous asymmetric epoxidation of unfunctionalized olefins catalyzed by polymer-bound (salen)manganese complexes. Tetrahedron: Asymmetry,1996,7(8):2293-2302
[91]Park D W, Choi S D, Choi S J, et al. Asymmetric epoxidation of styrene on the heterogenized chiral salen complexes prepared from organo-functionalized mesoporous materials. Catal Lett,2002,78(1-4):145-151
[92]Yu K, Gu Z C, Ji R N, et al. Heterogeneous chiral Mn(Ⅲ) salen catalysts for the epoxidation of unfunctionalized olefins immobilized on mesoporous materials with different pore sizes. Tetrahedron,2009,65(1):305-311
[93]Tang X S, Tang Y H, Xu G J, et al. Highly enantioselective epoxidation of styrene and alpha-methylstyrene catalyzed by new doubly-immobilized chiral (salen)Mn(Ⅲ) catalysts. Catal Commun,2008,10(3):317-320
[94]Kowalak S, Weiss R C, Balkus K J. Zeolite encapsulated Pd(salen), a selective hydrogenation catalyst. J Chem Soc, Chem Commun,1991, (1):57-58
[95]Ulagappan N, Krishnasamy V. Synthesis, characterization and phenol hydroxylation reaction of zeolite-Y encapsulated metal-salen complexes. India J Chem, Sect A,1996,35(9): 787-789
[96]Bessel C A, Rolison D R. Electrocatalytic reactivity of zeolite-encapsulated Co(salen) with benzyl chloride. J Am Chem Soc,1997,119(51):12673-12674
[97]Ogunwumi S B, Bein T. Intrazeolite assembly of a chiral manganese salen epoxidation catalyst. Chem Commun,1997, (9):901-902
[98]Sabater M J, Corma A, Domenech A, et al. Chiral salen manganese complex encapsulated within zeolite Y:A heterogeneous enantioselective catalyst for the epoxidation of alkenes. Chem Commun,1997, (14):1285-1286
[99]Kahlen W, Wagner H H, Holderich W E. Zeolite effect in the enantioselective transhydrogenation over a Co-salen "ship-in-the-bottle" complex. Catal Lett,1998,54(1-2): 85-89
[100]Gbery G, Zsigmond A, Balkus K, Jr. Enantioselective epoxidations catalyzed by zeolite MCM-22 encapsulated Jacobsen's catalyst. Catal Lett,2001,74(1-2):77-80
[101]Heinrichs C, Holderich W. Novel zeolitic hosts for "ship-in-a-bottle" catalysts. Catal Lett, 1999,58(2-3):75-80
[102]Schuster C, Mollmann E, Tompos A, et al. Highly stereoselective epoxidation of (-)-α-pinene over chiral transition metal (salen) complexes occluded in zeolitic hosts. Catal Lett, 2001,74(1-2):69-75
[103]Yang H Q, Zhang L, Su W G, et al. Asymmetric ring-opening of epoxides on chiral Co(Salen) catalyst synthesized in SBA-16 through the "ship in a bottle" strategy. J Catal,2007, 248(2):204-212
[104]Yang H Q, Zhang L, Wang P, et al. The enantioselective cyanosilylation of aldehydes on a chiral VO(Salen) complex encapsulated in SBA-16. Green Chem,2009,11(2):257-264
[105]Yang H, Li J, Yang J, et al. Asymmetric reactions on chiral catalysts entrapped within a mesoporous cage. Chem Commun,2007,0(10):1086-1088
[106]Yang H, Zhang L, Zhong L, et al. Enhanced Cooperative Activation Effect in the Hydrolytic Kinetic Resolution of Epoxides on [Co(salen)] Catalysts Confined in Nanocages. Angewandte Chemie,2007,119(36):6985-6989
[107]Song Y M, Yao X Q, Chen H L, et al. Highly enantioselective epoxidation of unfunctionalized olefins catalyzed by a novel recyclable chiral poly-salen-Mn(III) complex. J Chem Soc, Perkin Trans 1,2002, (7):870-873
[108]Kureshy R I, Khan N U H, Abdi S H R, et al. Enantioselective epoxidation of nonfunctionalized alkenes catalyzed by recyclable new homochiral dimeric Mn(III) salen complexes. J Catal,2004,224(2):229-235
[109]Kureshy R I, Khan N U H, Abdi S H R, et al. Catalytic asymmetric epoxidation of non-functionalised alkenes using polymeric Mn(III) Salen as catalysts and NaOCl as oxidant. J Mol Catal A:Chem,2004,218(2):141-146
[110]Kureshy R I, Prathap K J, Singh S, et al. Chiral recyclable dimeric and polymeric Cr(III) salen complexes catalyzed aminolytic kinetic resolution of trans-aromatic epoxides under microwave irradiation. Chirality,2007,19(10):809-815
[111]Kureshy R I, Ahmad I, Pathak K, et al. Easily recyclable chiral polymeric Mn(III) salen complexes for oxidative kinetic resolution of racemic secondary alcohols. Chirality,2007,19(5): 352-357
[112]Pathak K, Bhatt A P, Abdi S H R, et al. Enantioselective phenylacetylene addition to aldehydes and ketones catalyzed by recyclable polymeric Zn(salen) complex. Chirality,2007, 19(1):82-88
[113]Khan N U H, Agrawal S, Kureshy R I, et al. Enantioselective Cyanoformylation of Aldehydes Catalyzed with Solid Base Mediated Chiral V(V) Salen Complexes. Chirality,2010, 22(1):153-158
[114]Kureshy R I, Kumar M, Agrawal S, et al. Enantioselective Desymmetrization of meso-Epoxides with Anilines Catalyzed by Polymeric and Monomeric Ti(Ⅳ) Salen Complexes. Chirality,2011,23(1):76-83
[115]Khan N U H, Saravanan S, Kureshy R I, et al. Asymmetric addition of trimethylsilylcyanide to N-benzylimines catalyzed by recyclable chiral dimeric Ⅴ(Ⅴ) salen complex. J Organomet Chem,2010,695(8):1133-1137
[116]Khan N-u H, Saravanan S, Kureshy R I, et al. Mn(Ⅲ) salen complexes-catalyzed enantioselective addition of trimethyl silylcyanide to N-benzylimines in the presence of 4-phenyl pyridine-N-oxide as an additive. Tetrahedron:Asymmetry,2010,21(17):2076-2080
[117]Kureshy R I, Khan N-u H, Abdi S H R, et al. Enantioselective epoxidation of non-functionalised alkenes using a urea-hydrogen peroxide oxidant and a dimeric homochiral Mn(Ⅲ)-Schiff base complex catalyst. Tetrahedron:Asymmetry,2001,12(3):433-437
[118]Pathak K, Ahmad I, Abdi S H R, et al. Oxidative kinetic resolution of racemic secondary alcohols catalyzed by recyclable chiral dimeric Mn(Ⅲ) salen catalysts. J Mol Catal A:Chem, 2007,274(1-2):120-126
[119]Tan R, Yin D H, Yu N Y, et al. A novel polymeric chiral salen Mn(Ⅲ) complex as solvent-regulated phase transfer catalyst in the asymmetric epoxidation of styrene. J Mol Catal A: Chem,2006,259(1-2):125-132
[120]Martinez A, Hemmert C, Meunier B. A macrocyclic chiral manganese(Ⅲ) Schiff base complex as an efficient catalyst for the asymmetric epoxidation of olefins. J Catal,2005,234(2): 250-255
[121]Maity N C, Abdi S H R, Kureshy R I, et al. Chiral macrocyclic salen Mn(Ⅲ) complexes catalyzed enantioselective epoxidation of non-functionalized alkenes using NaOCl and urea H2O2 as oxidants. J Catal,2011,277(1):123-127
[122]Kureshy R I, Roy T, Khan N-u H, et al. Reusable chiral macrocyclic Mn(Ⅲ) salen complexes for enantioselective epoxidation of nonfunctionalized alkenes. J Catal,2012,286(0): 41-50
[123]Khan N U H, Sadhukhan A, Maity N C, et al. Enantioselective O-acetylcyanation/cyanoformylation of aldehydes using catalysts with built-in crown ether-like motif in chiral macrocyclic Ⅴ(Ⅴ) salen complexes. Tetrahedron,2011,67(37):7073-7080
[124]Kureshy R I, Das A, Khan N U, et al. Cu(Ⅱ)-Macrocylic H-4 Salen Catalyzed Asymmetric Nitroaldol Reaction and Its Application in the Synthesis of alpha 1-Adrenergic Receptor Agonist (R)-Phenylephrine. Acs Catalysis,2011,1(11):1529-1535
[125]Kureshy R I, Dangi B, Das A, et al. Recyclable Cu(Ⅱ)-macrocyclic salen complexes catalyzed nitroaldol reaction of aldehydes:A practical strategy in the preparation of (R)-phenylephrine. Appl Catal A:Gen,2012,439:74-79
[126]Sadhukhan A, Khan N U H, Roy T, et al. Asymmetric Hydrolytic Kinetic Resolution with Recyclable Macrocyclic CoⅢ-Salen Complexes:A Practical Strategy in the Preparation of (R)-Mexiletine and (S)-Propranolol. Chem Eur J,2012,18(17):5256-5260
[127]Kureshy R I, Prathap K J, Kumar M, et al. Synthesis of enantiopure beta-amino alcohols via AKR/ARO of epoxides using recyclable macrocyclic Cr(III) salen complexes. Tetrahedron, 2011,67(43):8300-8307
[128]Maity N C, Rao G V S, Prathap K J, et al. Organic carbonates as solvents in macrocyclic Mn(III) salen catalyzed asymmetric epoxidation of non-functionalized olefins. J Mol Catal A: Chem,2013,366(0):380-389
[129]Tan R, Yin D H, Yu N Y, et al. Ionic liquid-functionalized salen Mn(III) complexes as tunable separation catalysts for enantioselective epoxidation of styrene. J Catal,2008,255(2): 287-295
[130]Tan R, Yin D H, Yu N Y, et al. Easily recyclable polymeric ionic liquid-functionalized chiral salen Mn(Ⅲ) complex for enantioselective epoxidation of styrene. J Catal,2009,263(2): 284-291
[131]Li C Y, Zhao J F, Tan R, et al. Recyclable ionic liquid-bridged chiral dimeric salen Mn(Ⅲ) complexes for oxidative kinetic resolution of racemic secondary alcohols. Catal Commun,2011, 15(1):27-31
[132]Kureshy R I, Khan N U H, Abdi S H R, et al. Enantioselective epoxidation of chromenes using chiral Mn(Ⅲ) salen catalysts with built-in phase-transfer capability. Tetrahedron Lett,2002, 43(14):2665-2668
[133]Kureshy R I, Khan N-u H, Abdi S H R, et al. A Highly Potential Analogue of Jacobsen Catalyst with In-built Phase Transfer Capability in Enantioselective Epoxidation of Nonfunctionalized Alkenes. J Catal,2002,209(1):99-104
[134]Luo R C, Tan R, Peng Z G, et al. Stable chiral salen Mn(III) complexes with built-in phase-transfer capability for the asymmetric epoxidation of unfunctionalized olefins using NaOCl as an oxidant. J Catal,2012,287(1):170-177
[135]Tan R, Yin D, Yu N, et al. Self-assembled Solvent-regulated Phase Transfer Catalyst for Epoxidation of Non-functionalized Alkenes. Catal Lett,2009,129(3-4):471-477
[136]Shultz A M, Sarjeant A A, Farha O K, et al. Post-Synthesis Modification of a Metal-Organic Framework To Form Metallosalen-Containing MOF Materials. J Am Chem Soc, 2011,133(34):13252-13255
[137]Shultz A M, Farha O K, Adhikari D, et al. Selective Surface and Near-Surface Modification of a Noncatenated, Catalytically Active Metal-Organic Framework Material Based on Mn(salen) Struts. Inorg Chem,2011,50(8):3174-3176
[138]Zhu C F, Yuan G Z, Chen X, et al. Chiral Nanoporous Metal-Metallosalen Frameworks for Hydrolytic Kinetic Resolution of Epoxides. J Am Chem Soc,2012,134(19):8058-8061
[139]Casiraghi G, Casnati G, Cornia M, et al. Selective reactions using metal phenoxides. Part 1. Reactions with formaldehyde. J Chem Soc, Perkin Trans 1,1978,0(4):318-321
[140]Canali L, Cowan E, Deleuze H, et al. Polystyrene and polymethacrylate resin-supported Jacobsen's alkene epoxidation catalyst. J Chem Soc, Perkin Trans 1,2000,0(13):2055-2066
[141]Larrow J F, Jacobsen E N, Gao Y, et al. A Practical Method for the Large-Scale Preparation of [N,N'-Bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]manganese(Ⅲ) chloride, a Highly Enantioselective Epoxidation Catalyst. J Org Chem,1994,59(7):1939-1942
[142]Beck J S, Vartuli J C, Roth W J, et al. A new family of mesoporous molecular sieves prepared with liquid crystal templates. J Am Chem Soc,1992,114(27):10834-10843
[143]Kresge C T, Leonowicz M E, Roth W J, et al. Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism. Nature,1992,359(6397):710-712
[144]Li C. Chiral Synthesis on Catalysts Immobilized in Microporous and Mesoporous Materials. Catal Rev-Sci Eng,2004,46(3-4):419-492
[145]Zhao D, Feng J, Huo Q, et al. Triblock Copolymer Syntheses of Mesoporous Silica with Periodic 50 to 300 Angstrom Pores. Science,1998,279(5350):548-552
[146]Holbach M, Weck M. Modular approach for the development of supported, monofunctionalized, salen catalysts. J Org Chem,2006,71(5):1825-1836
[147]Feth M P, Bolm C, Hildebrand J P, et al. Structural Investigation of High-Valent Manganese-Salen Complexes by UV/Vis, Raman, XANES, and EXAFS Spectroscopy. Chem Eur J,2003,9(6):1348-1359
[148]McGarrigle E M, Gilheany D G. Chromium-and Manganese-salen Promoted Epoxidation of Alkenes. Chem Rev,2005,105(5):1563-1602
[149]Hughes D L, Smith G B, Liu J, et al. Mechanistic Study of the Jacobsen Asymmetric Epoxidation of Indene. J Org Chem,1997,62(7):2222-2229
[150]Zhang W, Jacobsen E N. Asymmetric olefin epoxidation with sodium-hypochlorite catalyzed by easlily prepared chiral Mn(III) salen complexes. J Org Chem,1991,56(7): 2296-2298
[151]Palucki M, Pospisil P J, Zhang W, et al. Highly Enantioselective, Low-Temperature Epoxidation of Styrene. J Am Chem Soc,1994,116(20):9333-9334
[152]Silva A R, Vital J, Figueiredo J L, et al. Activated carbons with immobilised manganese(Ⅲ) salen complexes as heterogeneous catalysts in the epoxidation of olefins:influence of support and ligand functionalisation on selectivity and reusability. New J Chem,2003,27(10): 1511-1517
[153]Silva A R, Freitas M M A, Freire C, et al. Heterogenization of a Functionalized Copper(II) Schiff Base Complex by Direct Immobilization onto an Oxidized Activated Carbon. Langmuir, 2002,18(21):8017-8024
[154]Zhang C, Liang X, Liu S. Hydrogen production by catalytic dehydrogenation of methylcyclohexane over Pt catalysts supported on pyrolytic waste tire char. Int J Hydrogen Energy,2011,36(15):8902-8907
[155]Figueiredo J L, Pereira M F R, Freitas M M A, et al. Modification of the surface chemistry of activated carbons. Carbon,1999,37(9):1379-1389
[156]Domenech A, Formentin P, Garcia H, et al. Combined Electrochemical and EPR Studies of Manganese Schiff Base Complexes Encapsulated within the Cavities of Zeolite Y. Eur J Inorg Chem,2000,2000(6):1339-1344
[157]Baleizao C, Garcia H. Chiral salen complexes:An overview to recoverable and reusable homogeneous and heterogeneous catalysts. Chem Rev,2006,106(9):3987-4043
[158]Trindade A F, Gois P M P, Afonso C A M. Recyclable Stereoselective Catalysts. Chem Rev, 2009,109(2):418-514
[159]Kureshy R I, Khan N U H, Abdi S H R, et al. Enantioselective epoxidation of non-functionalised alkenes catalysed by dimeric homochiral Mn(III) Salen complex using oxone as oxidant. J Mol Catal A:Chem,2003,203(1-2):69-73
[160]Xia Q H, Ge H Q, Ye C P, et al. Advances in Homogeneous and Heterogeneous Catalytic Asymmetric Epoxidation. Chem Rev,2005,105(5):1603-1662
[2]Yamada S. Recent aspects of the stereochemistry of schiff-base-metal complexes. Coord Chem Rev,1966,1(4):415-437
[3]Atwood D A, Harvey M J. Group 13 Compounds Incorporating Salen Ligands. Chem Rev, 2000,101(1):37-52
[4]Dzugan S J, Goedken V L. Factors affecting aluminum-carbon bond reactivity of tetradentate Schiff-base organoaluminum complexes. Inorg Chem,1986,25(16):2858-2864
[5]Atwood D A, Hill M S, Jegier J A, et al. The Use of Five-Coordinate Aluminum Alkyls To Prepare Molecules Containing a Single Al-O-Si Linkage. Organometallics,1997,16(12): 2659-2664
[6]Carbonaro L, Isola M, La Pegna P, et al. Spectrophotometric Study of the Equilibria between Nickel(Ⅱ) Schiff-Base Complexes and Alkaline Earth or Nickel(II) Cations in Acetonitrile Solution. Inorg Chem,1999,38(24):5519-5525
[7]Sanchez M, Harvey M J, Nordstrom F, et al. Salen-Type Compounds of Calcium and Strontium. Inorg Chem,2002,41(21):5397-5402
[8]Haak R M, Decortes A, Escudero-Adan E C, et al. Shape-Persistent Octanuclear Zinc Salen Clusters:Synthesis, Characterization, and Catalysis. Inorg Chem,2011,50(17):7934-7936
[9]Feng W, Zhang Y, Zhang Z, et al. Anion-Induced Self-Assembly of Luminescent and Magnetic Homoleptic Cyclic Tetranuclear Ln4(Salen)4 and Ln4(Salen)2 Complexes (Ln= Nd, Yb, Er, or Gd). Inorg Chem,2012,51(21):11377-11386
[10]Thurston J H, Tang C G Z, Trahan D W, et al. Toward Rational Control of Metal Stoichiometry in Heterobimetallic Coordination Complexes:Synthesis and Characterization of Pb(Hsal)2(Cu(salen*))2, [Pb(NO3)(Cu(salen*))2](NO3), Pb(OAc)2(Cu(salen*)), and [Pb(OAc)(Ni(salen*))2](OAc). Inorg Chem,2004,43(8):2708-2713
[11]Wei P, Atwood D A. Bimetallic Borate Derivatives of the Salen Ligands. Inorg Chem,1997, 36(18):4060-4065
[12]El-Behery M, El-Twigry H. Synthesis, magnetic, spectral, and antimicrobial studies of Cu(Ⅱ), Ni(Ⅱ) Co(Ⅱ), Fe(Ⅲ), and UO2(Ⅱ) complexes of a new Schiff base hydrazone derived from 7-chloro-4-hydrazinoquinoline. Spectrochim Acta, Part A,2007,66(1):28-36
[13]Li T-R, Yang Z-Y, Wang B-D. Synthesis, Characterization and Antioxidant Activity of Naringenin Schiff Base and Its Cu(II), Ni(II), Zn(II) Complexes. Chem Pharm Bull,2007,55(1): 26-28
[14]Pandya N, Khan N-u H, Prathap K J, et al. DNA Binding, Antioxidant Activity, and DNA Damage Protection of Chiral Macrocyclic Mn(Ⅲ) Salen Complexes. Chirality,2012,24(12): 1063-1073
[15]Reddy P R, Shilpa A. Synthesis, Characterization, and DNA-Binding and-Cleavage Properties of Dinuclear Cu-II-Salophen/Salen Complexes. Chem Biodivers,2011,8(7): 1245-1265
[16]Khan N-u H, Pandya N, Kumar M, et al. Influence of chirality using Mn(iii) salen complexes on DNA binding and antioxidant activity. Org Biomol Chem,2010,8(19):4297-4307
[17]Peng B, Zhou W H, Yan L, et al. DNA-binding and cleavage studies of chiral Mn(III) salen complexes. Transition Met Chem,2009,34(2):231-237
[18]Khan N U H, Pandya N, Kureshy R I, et al. Synthesis, characterization, DNA binding and cleavage studies of chiral Ru(II) salen complexes. Spectrochim. Acta, Part A,2009,74(1): 113-119
[19]Ansari K I, Grant J D, Woldemariam G A, et al. Iron(III)-salen complexes with less DNA cleavage activity exhibit more efficient apoptosis in MCF7 cells. Org Biomol Chem,2009,7(5): 926-932
[20]Clever G H, Soltl Y, Burks H, et al. Metal-salen-base-pair complexes inside DNA: Complexation overrides sequence information. Chem Eur J,2006,12(34):8708-8718
[21]Verquin G, Fontaine G, Bria M, et al. DNA modification by oxovanadium(IV) complexes of salen derivatives. J Biol Inorg Chem,2004,9(3):345-353
[22]Brown R S, Nielsen M, Gothelf K V. Self-assembly of aluminium-salen coupled nanostructures from encoded modules with cleavable disulfide DNA-linkers. Chem Commun, 2004, (13):1464-1465
[23]Zhou X, Shearer J, Rokita S E. A Ni(salen)-biotin conjugate for rapid isolation of accessible DNA. J Am Chem Soc,2000,122(37):9046-9047
[24]Cheng C C, Lu Y L. Novel water-soluble 4,4-disubstituted ruthenium(III)-salen complexes in DNA stranded scission. J Chin Chem Soc,1998,45(5):611-617
[25]Routier S, Bernier J L, Waring M J, et al. Synthesis of a functionalized salen copper complex and its interaction with DNA. J Org Chem,1996,61(7):2326-2331
[26]Srinivasan K, Michaud P, Kochi J K. Epoxidation of olefins with cationic (salen)MnⅢ complexes-the modulation of catalytic activity by substituents. J Am Chem Soc,1986,108(9): 2309-2320
[27]Rihter B, Masnovi J. Oxidation of alkynes and ylides by oxo(salen)chromium(V) (salen=N,N'-ethylenebis-salicylideneiminato) trifluoromethanesulphonate. J Chem Soc, Chem Commun,1988, (1):35-37
[28]Finashina E D, Kramareva N V, Kustov L M. Oxidation of catecholamines on chitosan-immobilized Co(Ⅱ) salen complexes. Macromol Symp,2003,204(1):205-217
[29]Kervinen K, Kopi H, Leskela M, et al. Oxidation of veratryl alcohol by molecular oxygen in aqueous solution catalyzed by cobalt salen-type complexes:the effect of reaction conditions. J Mol Catal A:Chem,2003,203(1-2):9-19
[30]Milo A, Neumann R. An achiral manganese salen catalyst encapsulated in a peptidic phosphonate homochiral solid for the enantioselective formation of diols by consecutive epoxidation and hydration reactions. Chem Commun,2011,47(9):2535-2537
[31]Li B, Bai S, Wang X, et al. Hydration of Epoxides on [CoⅢ(salen)] Encapsulated in Silica-Based Nanoreactors. Angew Chem Int Ed,2012,51(46):11517-11521
[32]Paddock R L, Nguyen S T. Chemical CO2 Fixation:Cr(Ⅲ) Salen Complexes as Highly Efficient Catalysts for the Coupling of CO2 and Epoxides. J Am Chem Soc,2001,123(46): 11498-11499
[33]Darensbourg D J, Billodeaux D R. Aluminum Salen Complexes and Tetrabutylammonium Salts:A Binary Catalytic System for Production of Polycarbonates from CO2 and Cyclohexene Oxide. Inorg Chem,2005,44(5):1433-1442
[34]Alvaro M, Baleizao C, Carbonell E, et al. Polymer-bound aluminium salen complex as reusable catalysts for CO2 insertion into epoxides. Tetrahedron,2005,61(51):12131-12139
[35]We R, Noda K, Ito Y, et al. Enantioselective epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes. Tetrahedron Lett,1991,32(8):1055-1058
[36]Zhang W, Loebach J L, Wilson S R, et al. Enantioselective epoxidation of unfunctionalized olefins catalyzed by salen manganese complexes. J Am Chem Soc,1990,112(7):2801-2803
[37]Palucki M, Hanson P, Jacobsen E N. Asymmetric oxidation of sulfides with H2O2 catalyzed by (salen)Mn(III) complexes. Tetrahedron Lett,1992,33(47):7111-7114
[38]Sun W, Wang H W, Xia C Q et al. Chiral-Mn(salen)-complex-catalyzed kinetic resolution of secondary alcohols in water. Angew Chem Inter Ed,2003,42(9):1042-+
[39]Tokunaga M, Larrow J F, Kakiuchi F, et al. Asymmetric Catalysis with Water:Efficient Kinetic Resolution of Terminal Epoxides by Means of Catalytic Hydrolysis. Science,1997, 277(5328):936-938
[40]Bartoli G, Bosco M, Carlone A, et al. Asymmetric Catalytic Synthesis of Enantiopure N-Protected 1,2-Amino Alcohols. Org Lett,2004,6(22):3973-3975
[41]Bartoli G, Bosco M, Carlone A, et al. Asymmetric Aminolysis of Aromatic Epoxides:A Facile Catalytic Enantioselective Synthesis of anti-β-Amino Alcohols. Org Lett,2004,6(13): 2173-2176
[42]Loy R N, Jacobsen E N. Enantioselective Intramolecular Openings of Oxetanes Catalyzed by (salen)Co(III) Complexes:Access to Enantioenriched Tetrahydrofurans. J Am Chem Soc, 2009,131(8):2786-2787
[43]Belokon Y N, Green B, Ikonnikov N S, et al. The asymmetric addition of trimethylsilyl cyanide to ketones catalysed by a bimetallic, chiral (salen)titanium complex. Tetrahedron Lett, 1999,40(46):8147-8150
[44]Kim S S, Lee S H, Kwak J M. Enantioselective cyanosilylation of ketones catalyzed by Mn(salen)/Ph3PO. Tetrahedron:Asymmetry,2006,17(8):1165-1169
[45]Kim S S, Kwak J M. Asymmetric addition of trimethylsilyl cyanide to ketones catalyzed by Al(salen)/triphenylphosphine oxide. Tetrahedron,2006,62(1):49-53
[46]Cozzi P G, Papa A, Umani-Ronchi A. Enantioselective addition of Et2Zn to aldehydes promoted by a chiral Schiff base metal complex. Tetrahedron Lett,1996,37(26):4613-4616
[47]Cozzi P G Enantioselective Alkynylation of Ketones Catalyzed by Zn(Salen) Complexes. Angew Chem Int Ed,2003,42(25):2895-2898
[48]Park J, Lang K, Abboud K A, et al. Self-Assembled Dinuclear Cobalt(II)-Salen Catalyst Through Hydrogen-Bonding and Its Application to Enantioselective Nitro-Aldol (Henry) Reaction. J Am Chem Soc,2008,130(49):16484-16485
[49]Kogami Y, Nakajima T, Ashizawa T, et al. Enantioselective Henry Reaction Catalyzed by Optically Active Ketoiminatocobalt Complexes. Chem Lett,2004,33(5):614-615
[50]Frunza L, Kosslick H, Landmesser H, et al. Host/guest interactions in nanoporous materials I. The embedding of chiral salen manganese(III) complex into mesoporous silicates. J Mol Catal A:Chem,1997,123(2-3):179-187
[51]Piaggio P, McMorn P, Langham C, et al. Asymmetric epoxidation of stilbene by manganese(III) chiral salen complex immobilized in Al-MCM-41. New J Chem,1998,22(11): 1167-1169
[52]Kim G J, Kim S H. Immobilization of new Mn(salen) complex over MCM-41 and its activity in asymmetric epoxidation of styrene. Catal Lett,1999,57(3):139-143
[53]Piaggio P, Langham C, McMorn P, et al. Catalytic asymmetric epoxidation of stilbene using a chiral salen complex immobilized in Mn-exchanged Al-MCM-41. J Chem Soc, Perkin Trans 2, 2000, (1):143-148
[54]Kureshy R I, Khan N U H, Abdi S H R, et al. Dicationic chiral Mn(Ⅲ) salen complex exchanged in the interlayers of montmorillonite clay:a heterogeneous enantioselective catalyst for epoxidation of nonfunctionalized alkenes. J Catal,2004,221(1):234-240
[55]Das P, Kuzniarska-Biernacka I, Silva A R, et al. Encapsulation of chiral Mn(Ⅲ) salen complexes into aluminium pillared clays:Application as heterogeneous catalysts in the epoxidation of styrene. J Mol Catal A:Chem,2006,248(1-2):135-143
[56]Piaggio P, McMorn P, Murphy D, et al. Enantioselective epoxidation of (Z)-stilbene using a chiral Mn(Ⅲ)-salen complex:effect of immobilisation on MCM-41 on product selectivity. J Chem Soc, Perkin Trans 2,2000, (10):2008-2015
[57]Zhou X-G. Yu X-Q, Huang J-S, et al. Asymmetric epoxidation of alkenes catalysed by chromium binaphthyl Schiff base complex supported on MCM-41. Chem Commun,1999,0(18): 1789-1790
[58]Xiang S, Zhang Y L, Xin Q, et al. Enantioselective epoxidation of olefins catalyzed by Mn (salen)/MCM-41 synthesized with a new anchoring method. Chem Commun,2002, (22): 2696-2697
[59]Zhang H D, Xiang S, Li C. Enantioselective epoxidation of unfunctionalised olefins catalyzed by Mn(salen) complexes immobilized in porous materials via phenyl sulfonic group. Chem Commun,2005, (9):1209-1211
[60]Zhang H D, Xiang S, Xiao J L, et al. Heterogeneous enantioselective epoxidation catalyzed by Mn(salen) complexes grafted onto mesoporous materials by phenoxy group. J Mol Catal A: Chem,2005,238(1-2):175-184
[61]Zhang H D, Zhang Y M, Li C. Asymmetric epoxidation of unfunctionalized olefins catalyzed by Mn(salen) axially immobilized onto insoluble polymers. Tetrahedron:Asymmetry, 2005,16(14):2417-2423
[62]Shen H S, Fu X K, Bao H B, et al. Synthesis and characterization of a new kind of immobilized Mn(salen) and catalytic epoxidation of styrene on the catalyst. Polym Adv Technol, 2009,20(2):77-83
[63]Bai R F, Fu X K, Bao H B, et al. Chiral Salen Mn(III) complex axial coordination immobilized on diamine modified ZSPP and their catalytic epoxidation of styrene. Catal Commun,2008,9(7):1588-1594
[64]Huang J, Fu X K, Miao Q. Synthesis of a novel type of chiral salen Mn(III) complex immobilized on crystalline zinc poly(styrene-phenylvinylphosphonate)-phosphate (ZnPS-PVPP) as effective catalysts for asymmetric epoxidation of unfunctionalized olefins. Catal Sci Technol, 2011,1(8):1472-1482
[65]Huang J, Fu X K, Miao Q. Catalytic asymmetric epoxidation of unfunctionalized olefins using a series novel type of layered crystalline organic polymer-inorganic hybrid zinc phosphonate-phosphate immobilized aryldiamine modified chiral salen Mn(Ⅲ) complex. Appl Catal A:Gen,2011,407(1-2):163-172
[66]Hu X Y, Fu X K, Xu J W, et al. A novel layered organic polymer-inorganic hybrid zinc poly (styrene-phenylvinylphosphonate)-phosphate immobilized chiral salen Mn(Ⅲ) catalyst large-scale asymmetric epoxidation of unfunctionalized olefins. J Organomet Chem,2011, 696(15-16):2797-2804
[67]Liu Z J, Fu X K, Hu X Y, et al. Asymmetric epoxidation of unfunctionalized olefins catalyzed by chiral salen Mn(III) immobilized onto sulfoalkyl modified zirconium poly(styrene-isopropenyl phosphonate)-phosphate and zirconium poly(styrene-phenylvivyl phosphonate)-phosphate. J Organomet Chem,2012,713(1):157-162
[68]Huang J, Fu X K, Wang G, et al. A high efficient large-scale asymmetric epoxidation of unfunctionalized olefins employing a novel type of chiral salen Mn(III) immobilized onto layered crystalline aryldiamine modified zinc poly(styrene-phenylvinylphosphonate)-phosphate. J Mol Catal A:Chem,2012,357:162-173
[69]Luo Y F, Fu X K, Zou X C, et al. Effect of Axial Linker Group on Heterogeneous Chiral Salen Mn(III) Catalyzed Enantioselective Epoxidation of Unfunctionalized Olefins. Chin J Inorg Chem,2011,27(7):1302-1308
[70]Huang J, Fu X K, Wang C W, et al. Chiral salen Mn(Ⅲ) immobilized onto sulfoalkyl-modified zinc poly(styrene-phenylvinylphosphonate)-phosphate as effective catalysts for epoxidation of unfunctionalized olefins. Microporous Mesoporous Mater,2012,153(1): 294-301
[71]Jia Z Y, Fu X K, Luo Y F, et al. Chiral Salen Mn(Ⅲ) Complex Axial Coordination Immobilized on Diamine Modified Alspp and Highly Efficient Large-Scale Epoxidation of Olefins as a Recoverable Catalyst. J Inorg Organomet Polym Mater,2012,22(2):415-422
[72]Kim Y S, Guo X F, Kim G J. Highly active new chiral Co(Ⅲ) salen catalysts immobilized by electrostatic interaction with sulfonic acid linkages on ordered mesoporous SBA-16 silica. Chem Commun,2009, (28):4296-4298
[73]Gong B W, Fu X K, Chen J X, et al. Synthesis of a new type of immobilized chiral salen Mn(III) complex as effective catalysts for asymmetric epoxidation of unfunctionalized olefins. J Catal,2009,262(1):9-17
[74]Silva A R, Freire C, de Castro B. Jacobsen catalyst anchored onto an activated carbon as an enantioselective heterogeneous catalyst for the epoxidation of alkenes. Carbon,2004,42(14): 3027-3030
[75]Silva A R, Budarin V, Clark J H, et al. Chiral manganese(Ⅲ) Schiff base complexes anchored onto activated carbon as enantioselective heterogeneous catalysts for alkene epoxidation. Carbon,2005,43(10):2096-2105
[76]Tu X B, Fu X K, Hu X Y, et al. Chiral salen Mn(Ⅲ) immobilized on sulfoalkyl modified ZSP-IPPA as an effective catalyst for asymmetric epoxidation of unfunctionalized olefins. Inorg Chem Commun,2010,13(3):404-407
[77]Kim G J, Shin J H. The catalytic activity of new chiral salen complexes immobilized on MCM-41 by multi-step grafting in the asymmetric epoxidation. Tetrahedron Lett,1999,40(37): 6827-6830
[78]Kim G J, Park D W. The catalytic activity of new chiral salen complexes immobilized on MCM-41 in the asymmetric hydrolysis of epoxides to diols. Catal Today,2000,63(2-4):537-547
[79]Zhao D, Zhao J, Zhao S, et al. Preparation of MCM-41 supported heterogenized chiral Salen Mn (Ⅲ) complex and the catalytic activity in the asymmetric epoxidation. J Inorg Organomet Polym Mater,2007,17(4):653-659
[80]Dhahagani K, Rajesh J, Kannan R, et al. Asymmetric Henry reaction of aldehydes catalyzed by recyclable an MCM-41 supported copper(II) salen complex. Tetrahedron:Asymmetry,2011, 22(8):857-865
[81]Kureshy R I, Ahmad I, Khan N H, et al. Encapsulation of a chiral Mn-III(salen) complex in ordered mesoporous silicas:an approach towards heterogenizing asymmetric epoxidation catalysts for non-functionalized alkenes. Tetrahedron:Asymmetry,2005,16(21):3562-3569
[82]Kureshy R I, Ahmad I, Khan N H, et al. Chiral Mn(III) salen complexes covalently bonded on modified MCM-41 and SBA-15 as efficient catalysts for enantioselective epoxidation of nonfunctionalized alkenes. J Catal,2006,238(1):134-141
[83]Yu K, Gu Z, Ji R, et al. Effect of pore size on the performance of mesoporous material supported chiral Mn(III) salen complex for the epoxidation of unfunctionalized olefins. J Catal, 2007,252(2):312-320
[84]Bigi F, Moroni L, Maggi R, et al. Heterogeneous enantioselective epoxidation of olefins catalysed by unsymmetrical (salen) Mn(Ⅲ) complexes supported on amorphous or MCM-41 silica through a new triazine-based linker. Chem Commun,2002, (7):716-717
[85]Kuzniarska-Biernacka I, Silva A R, Carvalho A P, et al. Organo-laponites as novel mesoporous supports for manganese(Ⅲ) salen catalysts. Langmuir,2005,21(23):10825-10834
[86]Silva A R, Budarin V, Clark J H, et al. Organo-functionalized activated carbons as supports for the coyalent attachment of a chiral manganese(Ⅲ) salen complex. Carbon,2007,45(10): 1951-1964
[87]Roy T, Kureshy R I, Khan N, et al. Immobilized dimeric chiral Mn(Ⅲ) salen complex on short channel ordered mesoporous silica as an effective catalyst for the epoxidation of non-functionalized alkenes. Tetrahedron,2012,68(31):6314-6322
[88]Song C E, Roh E J, Yu B M, et al. Heterogeneous asymmetric epoxidation of alkenes catalysed by a polymer-bound (pyrrolidine salen)manganese(Ⅲ) complex. Chem Commun,2000, (7):615-616
[89]Silva A R, Wilson K, Clark J H, et al. Covalent attachment of chiral manganese(Ⅲ) salen complexes onto functionalised hexagonal mesoporous silica and application to the asymmetric epoxidation of alkenes. Microporous Mesoporous Mater,2006,91(1-3):128-138
[90]Minutolo F, Pini D, Petri A, et al. Heterogeneous asymmetric epoxidation of unfunctionalized olefins catalyzed by polymer-bound (salen)manganese complexes. Tetrahedron: Asymmetry,1996,7(8):2293-2302
[91]Park D W, Choi S D, Choi S J, et al. Asymmetric epoxidation of styrene on the heterogenized chiral salen complexes prepared from organo-functionalized mesoporous materials. Catal Lett,2002,78(1-4):145-151
[92]Yu K, Gu Z C, Ji R N, et al. Heterogeneous chiral Mn(Ⅲ) salen catalysts for the epoxidation of unfunctionalized olefins immobilized on mesoporous materials with different pore sizes. Tetrahedron,2009,65(1):305-311
[93]Tang X S, Tang Y H, Xu G J, et al. Highly enantioselective epoxidation of styrene and alpha-methylstyrene catalyzed by new doubly-immobilized chiral (salen)Mn(Ⅲ) catalysts. Catal Commun,2008,10(3):317-320
[94]Kowalak S, Weiss R C, Balkus K J. Zeolite encapsulated Pd(salen), a selective hydrogenation catalyst. J Chem Soc, Chem Commun,1991, (1):57-58
[95]Ulagappan N, Krishnasamy V. Synthesis, characterization and phenol hydroxylation reaction of zeolite-Y encapsulated metal-salen complexes. India J Chem, Sect A,1996,35(9): 787-789
[96]Bessel C A, Rolison D R. Electrocatalytic reactivity of zeolite-encapsulated Co(salen) with benzyl chloride. J Am Chem Soc,1997,119(51):12673-12674
[97]Ogunwumi S B, Bein T. Intrazeolite assembly of a chiral manganese salen epoxidation catalyst. Chem Commun,1997, (9):901-902
[98]Sabater M J, Corma A, Domenech A, et al. Chiral salen manganese complex encapsulated within zeolite Y:A heterogeneous enantioselective catalyst for the epoxidation of alkenes. Chem Commun,1997, (14):1285-1286
[99]Kahlen W, Wagner H H, Holderich W E. Zeolite effect in the enantioselective transhydrogenation over a Co-salen "ship-in-the-bottle" complex. Catal Lett,1998,54(1-2): 85-89
[100]Gbery G, Zsigmond A, Balkus K, Jr. Enantioselective epoxidations catalyzed by zeolite MCM-22 encapsulated Jacobsen's catalyst. Catal Lett,2001,74(1-2):77-80
[101]Heinrichs C, Holderich W. Novel zeolitic hosts for "ship-in-a-bottle" catalysts. Catal Lett, 1999,58(2-3):75-80
[102]Schuster C, Mollmann E, Tompos A, et al. Highly stereoselective epoxidation of (-)-α-pinene over chiral transition metal (salen) complexes occluded in zeolitic hosts. Catal Lett, 2001,74(1-2):69-75
[103]Yang H Q, Zhang L, Su W G, et al. Asymmetric ring-opening of epoxides on chiral Co(Salen) catalyst synthesized in SBA-16 through the "ship in a bottle" strategy. J Catal,2007, 248(2):204-212
[104]Yang H Q, Zhang L, Wang P, et al. The enantioselective cyanosilylation of aldehydes on a chiral VO(Salen) complex encapsulated in SBA-16. Green Chem,2009,11(2):257-264
[105]Yang H, Li J, Yang J, et al. Asymmetric reactions on chiral catalysts entrapped within a mesoporous cage. Chem Commun,2007,0(10):1086-1088
[106]Yang H, Zhang L, Zhong L, et al. Enhanced Cooperative Activation Effect in the Hydrolytic Kinetic Resolution of Epoxides on [Co(salen)] Catalysts Confined in Nanocages. Angewandte Chemie,2007,119(36):6985-6989
[107]Song Y M, Yao X Q, Chen H L, et al. Highly enantioselective epoxidation of unfunctionalized olefins catalyzed by a novel recyclable chiral poly-salen-Mn(III) complex. J Chem Soc, Perkin Trans 1,2002, (7):870-873
[108]Kureshy R I, Khan N U H, Abdi S H R, et al. Enantioselective epoxidation of nonfunctionalized alkenes catalyzed by recyclable new homochiral dimeric Mn(III) salen complexes. J Catal,2004,224(2):229-235
[109]Kureshy R I, Khan N U H, Abdi S H R, et al. Catalytic asymmetric epoxidation of non-functionalised alkenes using polymeric Mn(III) Salen as catalysts and NaOCl as oxidant. J Mol Catal A:Chem,2004,218(2):141-146
[110]Kureshy R I, Prathap K J, Singh S, et al. Chiral recyclable dimeric and polymeric Cr(III) salen complexes catalyzed aminolytic kinetic resolution of trans-aromatic epoxides under microwave irradiation. Chirality,2007,19(10):809-815
[111]Kureshy R I, Ahmad I, Pathak K, et al. Easily recyclable chiral polymeric Mn(III) salen complexes for oxidative kinetic resolution of racemic secondary alcohols. Chirality,2007,19(5): 352-357
[112]Pathak K, Bhatt A P, Abdi S H R, et al. Enantioselective phenylacetylene addition to aldehydes and ketones catalyzed by recyclable polymeric Zn(salen) complex. Chirality,2007, 19(1):82-88
[113]Khan N U H, Agrawal S, Kureshy R I, et al. Enantioselective Cyanoformylation of Aldehydes Catalyzed with Solid Base Mediated Chiral V(V) Salen Complexes. Chirality,2010, 22(1):153-158
[114]Kureshy R I, Kumar M, Agrawal S, et al. Enantioselective Desymmetrization of meso-Epoxides with Anilines Catalyzed by Polymeric and Monomeric Ti(Ⅳ) Salen Complexes. Chirality,2011,23(1):76-83
[115]Khan N U H, Saravanan S, Kureshy R I, et al. Asymmetric addition of trimethylsilylcyanide to N-benzylimines catalyzed by recyclable chiral dimeric Ⅴ(Ⅴ) salen complex. J Organomet Chem,2010,695(8):1133-1137
[116]Khan N-u H, Saravanan S, Kureshy R I, et al. Mn(Ⅲ) salen complexes-catalyzed enantioselective addition of trimethyl silylcyanide to N-benzylimines in the presence of 4-phenyl pyridine-N-oxide as an additive. Tetrahedron:Asymmetry,2010,21(17):2076-2080
[117]Kureshy R I, Khan N-u H, Abdi S H R, et al. Enantioselective epoxidation of non-functionalised alkenes using a urea-hydrogen peroxide oxidant and a dimeric homochiral Mn(Ⅲ)-Schiff base complex catalyst. Tetrahedron:Asymmetry,2001,12(3):433-437
[118]Pathak K, Ahmad I, Abdi S H R, et al. Oxidative kinetic resolution of racemic secondary alcohols catalyzed by recyclable chiral dimeric Mn(Ⅲ) salen catalysts. J Mol Catal A:Chem, 2007,274(1-2):120-126
[119]Tan R, Yin D H, Yu N Y, et al. A novel polymeric chiral salen Mn(Ⅲ) complex as solvent-regulated phase transfer catalyst in the asymmetric epoxidation of styrene. J Mol Catal A: Chem,2006,259(1-2):125-132
[120]Martinez A, Hemmert C, Meunier B. A macrocyclic chiral manganese(Ⅲ) Schiff base complex as an efficient catalyst for the asymmetric epoxidation of olefins. J Catal,2005,234(2): 250-255
[121]Maity N C, Abdi S H R, Kureshy R I, et al. Chiral macrocyclic salen Mn(Ⅲ) complexes catalyzed enantioselective epoxidation of non-functionalized alkenes using NaOCl and urea H2O2 as oxidants. J Catal,2011,277(1):123-127
[122]Kureshy R I, Roy T, Khan N-u H, et al. Reusable chiral macrocyclic Mn(Ⅲ) salen complexes for enantioselective epoxidation of nonfunctionalized alkenes. J Catal,2012,286(0): 41-50
[123]Khan N U H, Sadhukhan A, Maity N C, et al. Enantioselective O-acetylcyanation/cyanoformylation of aldehydes using catalysts with built-in crown ether-like motif in chiral macrocyclic Ⅴ(Ⅴ) salen complexes. Tetrahedron,2011,67(37):7073-7080
[124]Kureshy R I, Das A, Khan N U, et al. Cu(Ⅱ)-Macrocylic H-4 Salen Catalyzed Asymmetric Nitroaldol Reaction and Its Application in the Synthesis of alpha 1-Adrenergic Receptor Agonist (R)-Phenylephrine. Acs Catalysis,2011,1(11):1529-1535
[125]Kureshy R I, Dangi B, Das A, et al. Recyclable Cu(Ⅱ)-macrocyclic salen complexes catalyzed nitroaldol reaction of aldehydes:A practical strategy in the preparation of (R)-phenylephrine. Appl Catal A:Gen,2012,439:74-79
[126]Sadhukhan A, Khan N U H, Roy T, et al. Asymmetric Hydrolytic Kinetic Resolution with Recyclable Macrocyclic CoⅢ-Salen Complexes:A Practical Strategy in the Preparation of (R)-Mexiletine and (S)-Propranolol. Chem Eur J,2012,18(17):5256-5260
[127]Kureshy R I, Prathap K J, Kumar M, et al. Synthesis of enantiopure beta-amino alcohols via AKR/ARO of epoxides using recyclable macrocyclic Cr(III) salen complexes. Tetrahedron, 2011,67(43):8300-8307
[128]Maity N C, Rao G V S, Prathap K J, et al. Organic carbonates as solvents in macrocyclic Mn(III) salen catalyzed asymmetric epoxidation of non-functionalized olefins. J Mol Catal A: Chem,2013,366(0):380-389
[129]Tan R, Yin D H, Yu N Y, et al. Ionic liquid-functionalized salen Mn(III) complexes as tunable separation catalysts for enantioselective epoxidation of styrene. J Catal,2008,255(2): 287-295
[130]Tan R, Yin D H, Yu N Y, et al. Easily recyclable polymeric ionic liquid-functionalized chiral salen Mn(Ⅲ) complex for enantioselective epoxidation of styrene. J Catal,2009,263(2): 284-291
[131]Li C Y, Zhao J F, Tan R, et al. Recyclable ionic liquid-bridged chiral dimeric salen Mn(Ⅲ) complexes for oxidative kinetic resolution of racemic secondary alcohols. Catal Commun,2011, 15(1):27-31
[132]Kureshy R I, Khan N U H, Abdi S H R, et al. Enantioselective epoxidation of chromenes using chiral Mn(Ⅲ) salen catalysts with built-in phase-transfer capability. Tetrahedron Lett,2002, 43(14):2665-2668
[133]Kureshy R I, Khan N-u H, Abdi S H R, et al. A Highly Potential Analogue of Jacobsen Catalyst with In-built Phase Transfer Capability in Enantioselective Epoxidation of Nonfunctionalized Alkenes. J Catal,2002,209(1):99-104
[134]Luo R C, Tan R, Peng Z G, et al. Stable chiral salen Mn(III) complexes with built-in phase-transfer capability for the asymmetric epoxidation of unfunctionalized olefins using NaOCl as an oxidant. J Catal,2012,287(1):170-177
[135]Tan R, Yin D, Yu N, et al. Self-assembled Solvent-regulated Phase Transfer Catalyst for Epoxidation of Non-functionalized Alkenes. Catal Lett,2009,129(3-4):471-477
[136]Shultz A M, Sarjeant A A, Farha O K, et al. Post-Synthesis Modification of a Metal-Organic Framework To Form Metallosalen-Containing MOF Materials. J Am Chem Soc, 2011,133(34):13252-13255
[137]Shultz A M, Farha O K, Adhikari D, et al. Selective Surface and Near-Surface Modification of a Noncatenated, Catalytically Active Metal-Organic Framework Material Based on Mn(salen) Struts. Inorg Chem,2011,50(8):3174-3176
[138]Zhu C F, Yuan G Z, Chen X, et al. Chiral Nanoporous Metal-Metallosalen Frameworks for Hydrolytic Kinetic Resolution of Epoxides. J Am Chem Soc,2012,134(19):8058-8061
[139]Casiraghi G, Casnati G, Cornia M, et al. Selective reactions using metal phenoxides. Part 1. Reactions with formaldehyde. J Chem Soc, Perkin Trans 1,1978,0(4):318-321
[140]Canali L, Cowan E, Deleuze H, et al. Polystyrene and polymethacrylate resin-supported Jacobsen's alkene epoxidation catalyst. J Chem Soc, Perkin Trans 1,2000,0(13):2055-2066
[141]Larrow J F, Jacobsen E N, Gao Y, et al. A Practical Method for the Large-Scale Preparation of [N,N'-Bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]manganese(Ⅲ) chloride, a Highly Enantioselective Epoxidation Catalyst. J Org Chem,1994,59(7):1939-1942
[142]Beck J S, Vartuli J C, Roth W J, et al. A new family of mesoporous molecular sieves prepared with liquid crystal templates. J Am Chem Soc,1992,114(27):10834-10843
[143]Kresge C T, Leonowicz M E, Roth W J, et al. Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism. Nature,1992,359(6397):710-712
[144]Li C. Chiral Synthesis on Catalysts Immobilized in Microporous and Mesoporous Materials. Catal Rev-Sci Eng,2004,46(3-4):419-492
[145]Zhao D, Feng J, Huo Q, et al. Triblock Copolymer Syntheses of Mesoporous Silica with Periodic 50 to 300 Angstrom Pores. Science,1998,279(5350):548-552
[146]Holbach M, Weck M. Modular approach for the development of supported, monofunctionalized, salen catalysts. J Org Chem,2006,71(5):1825-1836
[147]Feth M P, Bolm C, Hildebrand J P, et al. Structural Investigation of High-Valent Manganese-Salen Complexes by UV/Vis, Raman, XANES, and EXAFS Spectroscopy. Chem Eur J,2003,9(6):1348-1359
[148]McGarrigle E M, Gilheany D G. Chromium-and Manganese-salen Promoted Epoxidation of Alkenes. Chem Rev,2005,105(5):1563-1602
[149]Hughes D L, Smith G B, Liu J, et al. Mechanistic Study of the Jacobsen Asymmetric Epoxidation of Indene. J Org Chem,1997,62(7):2222-2229
[150]Zhang W, Jacobsen E N. Asymmetric olefin epoxidation with sodium-hypochlorite catalyzed by easlily prepared chiral Mn(III) salen complexes. J Org Chem,1991,56(7): 2296-2298
[151]Palucki M, Pospisil P J, Zhang W, et al. Highly Enantioselective, Low-Temperature Epoxidation of Styrene. J Am Chem Soc,1994,116(20):9333-9334
[152]Silva A R, Vital J, Figueiredo J L, et al. Activated carbons with immobilised manganese(Ⅲ) salen complexes as heterogeneous catalysts in the epoxidation of olefins:influence of support and ligand functionalisation on selectivity and reusability. New J Chem,2003,27(10): 1511-1517
[153]Silva A R, Freitas M M A, Freire C, et al. Heterogenization of a Functionalized Copper(II) Schiff Base Complex by Direct Immobilization onto an Oxidized Activated Carbon. Langmuir, 2002,18(21):8017-8024
[154]Zhang C, Liang X, Liu S. Hydrogen production by catalytic dehydrogenation of methylcyclohexane over Pt catalysts supported on pyrolytic waste tire char. Int J Hydrogen Energy,2011,36(15):8902-8907
[155]Figueiredo J L, Pereira M F R, Freitas M M A, et al. Modification of the surface chemistry of activated carbons. Carbon,1999,37(9):1379-1389
[156]Domenech A, Formentin P, Garcia H, et al. Combined Electrochemical and EPR Studies of Manganese Schiff Base Complexes Encapsulated within the Cavities of Zeolite Y. Eur J Inorg Chem,2000,2000(6):1339-1344
[157]Baleizao C, Garcia H. Chiral salen complexes:An overview to recoverable and reusable homogeneous and heterogeneous catalysts. Chem Rev,2006,106(9):3987-4043
[158]Trindade A F, Gois P M P, Afonso C A M. Recyclable Stereoselective Catalysts. Chem Rev, 2009,109(2):418-514
[159]Kureshy R I, Khan N U H, Abdi S H R, et al. Enantioselective epoxidation of non-functionalised alkenes catalysed by dimeric homochiral Mn(III) Salen complex using oxone as oxidant. J Mol Catal A:Chem,2003,203(1-2):69-73
[160]Xia Q H, Ge H Q, Ye C P, et al. Advances in Homogeneous and Heterogeneous Catalytic Asymmetric Epoxidation. Chem Rev,2005,105(5):1603-1662
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |