有机膦小分子催化的基于aza-MBH反应的Domino反应研究
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摘要
Morita-Baylis-Hillman反应是指:在叔膦或者叔胺的催化下,醛与活泼双键的α位发生耦联得到一个具有多官能团的化合物的反应。该反应具有原子经济性,反应条件温和等优点,因此越来越受到化学家的重视。为了提高该反应的适用性,aza-MBH反应也被广泛的研究。本论文在第一章详细总结近年来aza-MBH反应的研究进展,在此基础上,我们设计并合成了一系列含有双官能团的有机膦催化剂,并且把这些催化剂应用到基于aza-MBH反应的Domino反应中。
首先我们合成了含有酚羟基的双官能团有机膦催化剂LBBA-1,并且把LBBA-1应用到丙烯醛与芳香醛的对甲基苯磺酰亚胺之间的反应。通过实验我们发现,如果在THF中进行该反应,反应能在1小时内高收率得到正常的aza-MBH加成产物。如果在氯仿中进行该反应,反应能在15分钟内以中等收率得到四氢吡啶衍生物。通过对该反应的机理仔细的研究发现,该反应经过了一个aza-MBH/Michael/Aodol/Dehydration Domino反应。并且为合成四氢吡啶衍生物提供了一种简单高效的方法。产物的结构通过单晶衍射,核磁,高分辨质谱的确证。
其次,通过对LBBA-1的研究发现,催化剂分子内的酚羟基不仪能加快反应速度,还能通过分子内氢键来稳定中间体。因此又设计并合成了亲核能力更强的催化剂LBBA-2,并且把LBBA-2应用到2,3-丁二烯酸酯与邻位含有酚羟基的硫代磷酰亚胺之间的反应。令我们惊奇的是,该反应既没有得到[3+2]反应的产物,也没有得到苯并吡喃衍生物。而是通过aza-MBH/umpolung Domino反应生成顺式2,3-取代苯并二氢呋喃衍生物。通过与三丁基膦的对比发现,催化剂分子内的酚羟基对于产物的构型是必要的。在此研究中,我们首次发现2,3-丁二烯酸酯可以作为一碳合成子用于有机合成,同时为顺式2,3-取代苯并二氢呋喃衍生物的合成提供了一种简单高效的合成方法。当用DMAP催化该反应时,如果亚胺苯环上含有吸电子基,得到的是苯并吡喃衍生物。如果苯环上含有供电子取代基,得到的是二氢苯并吡喃衍生物。产物的结构通过单晶衍射,核磁,高分辨质谱的确证。
再次,完成以上研究后,我们用4-甲基-2,3-丁二烯酸酯来代替上面反应中的2,3-丁二烯酸酯,结果发现,在LBBA-2的催化下,得到并不是取代的苯并二氢呋喃衍生物。而是苯并二氢吡喃衍生物,进一步的研究发现,在生成苯并二氢呋喃的反应中没有催化活性的三苯基膦,是该反应最有效的催化剂。当亚胺的苯环上含有吸电子取代基时,反应的选择性较好,主要得到顺式产物。当苯环的亚胺上含有供电子取代基时,得到的是顺式为主的顺反异构体的混合物。该反应是首次发现联烯的γ-甲基可以作为二碳合成子参与成环的反应。
最后,我们用LBBA-1和LBBA-2对于MBH,aza-MBH反应进行了研究,结果发现,由于该双官能团催化剂分子内既存在着路易斯碱又存在着布朗斯特酸,因此对于芳香醛与甲基乙烯基酮或者丙烯酸酯之间的反应是有效的催化剂,同时也能高效的催化水杨醛硫代磷酰亚胺与甲基乙烯基酮之间的aza-MBH反应。
Morita-Baylis-Hillman reaction:Tertiary phosphine or tertiary amine catalyzed coupling of aldehydes and activated olefins atαposition to give the highly functionlized products.This reaction has become one of the most extensively studied topics in organic chemistry,due to its inherently atom economic and mild reaction conditions.Considerable efforts have been made to expand its scope of application.In this thesis,included are the advanced of Morita-Baylis-Hillman detailedly summarized and our work on the design and syntheses of bifunctional phosphine catalyst,as well as their application to the MBH-based Domino reaction.
We have synthesized a LBBA-1 containing the OH,and applied it to the reaction of acrolein and imines.According to our experimental results,if THF was employed as solvent,traditional aza-MBH products could be obtained in high yield in one hour, while with CHCl_3 as solvent,tetrahydropyridine derivative as final products were afforded in moderate yield within 15 min.The investigations of the mechanism revealed that an aza-MBH/Michael/Aodol/Dehydration Domino reaction are involved.This reaction can serve as a concise and effective method for the synthesis of tetrahydropyridine derivatives.Structures of all the products were confirmed by X-ray,NMR and HRMS.
Studies of the LBBA-1 suggested that the OH of this catalyst not only accelerated the reaction,but also stabilized the intermediate via intramolecular hydrogen bond.Thus,we have designed and synthesized a more nucleophilic one, LBBA-2,and applied it to the reaction of 2,3-butadienoate and salicyl N-thiophosphinylimines.However neither the[3+2]compound nor the chromenes reported by shi was observed.As a matter of fact,an aza-MBH/umpolung domino reaction had taken placed and given the cis-2,3-dihydrobenzofurans.Compared with the ~nBu_3P,the OH is critical for the products' configuration.2,3-butadienoate acted as a one carbon synthon in this reaction,which was rarely reported.In the presence of DMAP,chromans and chromenes were obtained,respectively,for the imines with the electron-withdrawing groups and the ones with electron-donating groups.Structures of all the products are confirmed by X-ray,NMR and HRMS.
If 2,3-pentadienoate rather than 2,3-pentadienoate was employed,in the presence of LBBA-2 as catalyst,Chromans instead of dihydrobenzofurans were obtained.But the yields of product were unsatisfied.Further investigations shown that PPh_3,which proved to be ineffective catalyst in the formation of dihydrobenzofurans,serves as the most effective one in this reaction.For the imines bearing electron-withdrawing groups on the phenyl ring,cis products were obtained with well selectivity.In contrast,for their counterparts with electron-donating groups,cis and trans mixtures are obtained.This is the first case where theγ-methyl of allene is involved in the cycloation and thus serves as two carbon synthon.
LBBA-1 and LBBA-2 are highly effective catalysts for the MBH,aza-MBH reaction.Due to the coexistence of Lewis base and Bronsted acid,they can effectively catalyze the reactions between aldehydes and methyl vinyl ketone(MVK)/acrylate,as well as the aza-MBH reactions between MVK and salicyl N-thiophosphinyl imines.
首先我们合成了含有酚羟基的双官能团有机膦催化剂LBBA-1,并且把LBBA-1应用到丙烯醛与芳香醛的对甲基苯磺酰亚胺之间的反应。通过实验我们发现,如果在THF中进行该反应,反应能在1小时内高收率得到正常的aza-MBH加成产物。如果在氯仿中进行该反应,反应能在15分钟内以中等收率得到四氢吡啶衍生物。通过对该反应的机理仔细的研究发现,该反应经过了一个aza-MBH/Michael/Aodol/Dehydration Domino反应。并且为合成四氢吡啶衍生物提供了一种简单高效的方法。产物的结构通过单晶衍射,核磁,高分辨质谱的确证。
其次,通过对LBBA-1的研究发现,催化剂分子内的酚羟基不仪能加快反应速度,还能通过分子内氢键来稳定中间体。因此又设计并合成了亲核能力更强的催化剂LBBA-2,并且把LBBA-2应用到2,3-丁二烯酸酯与邻位含有酚羟基的硫代磷酰亚胺之间的反应。令我们惊奇的是,该反应既没有得到[3+2]反应的产物,也没有得到苯并吡喃衍生物。而是通过aza-MBH/umpolung Domino反应生成顺式2,3-取代苯并二氢呋喃衍生物。通过与三丁基膦的对比发现,催化剂分子内的酚羟基对于产物的构型是必要的。在此研究中,我们首次发现2,3-丁二烯酸酯可以作为一碳合成子用于有机合成,同时为顺式2,3-取代苯并二氢呋喃衍生物的合成提供了一种简单高效的合成方法。当用DMAP催化该反应时,如果亚胺苯环上含有吸电子基,得到的是苯并吡喃衍生物。如果苯环上含有供电子取代基,得到的是二氢苯并吡喃衍生物。产物的结构通过单晶衍射,核磁,高分辨质谱的确证。
再次,完成以上研究后,我们用4-甲基-2,3-丁二烯酸酯来代替上面反应中的2,3-丁二烯酸酯,结果发现,在LBBA-2的催化下,得到并不是取代的苯并二氢呋喃衍生物。而是苯并二氢吡喃衍生物,进一步的研究发现,在生成苯并二氢呋喃的反应中没有催化活性的三苯基膦,是该反应最有效的催化剂。当亚胺的苯环上含有吸电子取代基时,反应的选择性较好,主要得到顺式产物。当苯环的亚胺上含有供电子取代基时,得到的是顺式为主的顺反异构体的混合物。该反应是首次发现联烯的γ-甲基可以作为二碳合成子参与成环的反应。
最后,我们用LBBA-1和LBBA-2对于MBH,aza-MBH反应进行了研究,结果发现,由于该双官能团催化剂分子内既存在着路易斯碱又存在着布朗斯特酸,因此对于芳香醛与甲基乙烯基酮或者丙烯酸酯之间的反应是有效的催化剂,同时也能高效的催化水杨醛硫代磷酰亚胺与甲基乙烯基酮之间的aza-MBH反应。
Morita-Baylis-Hillman reaction:Tertiary phosphine or tertiary amine catalyzed coupling of aldehydes and activated olefins atαposition to give the highly functionlized products.This reaction has become one of the most extensively studied topics in organic chemistry,due to its inherently atom economic and mild reaction conditions.Considerable efforts have been made to expand its scope of application.In this thesis,included are the advanced of Morita-Baylis-Hillman detailedly summarized and our work on the design and syntheses of bifunctional phosphine catalyst,as well as their application to the MBH-based Domino reaction.
We have synthesized a LBBA-1 containing the OH,and applied it to the reaction of acrolein and imines.According to our experimental results,if THF was employed as solvent,traditional aza-MBH products could be obtained in high yield in one hour, while with CHCl_3 as solvent,tetrahydropyridine derivative as final products were afforded in moderate yield within 15 min.The investigations of the mechanism revealed that an aza-MBH/Michael/Aodol/Dehydration Domino reaction are involved.This reaction can serve as a concise and effective method for the synthesis of tetrahydropyridine derivatives.Structures of all the products were confirmed by X-ray,NMR and HRMS.
Studies of the LBBA-1 suggested that the OH of this catalyst not only accelerated the reaction,but also stabilized the intermediate via intramolecular hydrogen bond.Thus,we have designed and synthesized a more nucleophilic one, LBBA-2,and applied it to the reaction of 2,3-butadienoate and salicyl N-thiophosphinylimines.However neither the[3+2]compound nor the chromenes reported by shi was observed.As a matter of fact,an aza-MBH/umpolung domino reaction had taken placed and given the cis-2,3-dihydrobenzofurans.Compared with the ~nBu_3P,the OH is critical for the products' configuration.2,3-butadienoate acted as a one carbon synthon in this reaction,which was rarely reported.In the presence of DMAP,chromans and chromenes were obtained,respectively,for the imines with the electron-withdrawing groups and the ones with electron-donating groups.Structures of all the products are confirmed by X-ray,NMR and HRMS.
If 2,3-pentadienoate rather than 2,3-pentadienoate was employed,in the presence of LBBA-2 as catalyst,Chromans instead of dihydrobenzofurans were obtained.But the yields of product were unsatisfied.Further investigations shown that PPh_3,which proved to be ineffective catalyst in the formation of dihydrobenzofurans,serves as the most effective one in this reaction.For the imines bearing electron-withdrawing groups on the phenyl ring,cis products were obtained with well selectivity.In contrast,for their counterparts with electron-donating groups,cis and trans mixtures are obtained.This is the first case where theγ-methyl of allene is involved in the cycloation and thus serves as two carbon synthon.
LBBA-1 and LBBA-2 are highly effective catalysts for the MBH,aza-MBH reaction.Due to the coexistence of Lewis base and Bronsted acid,they can effectively catalyze the reactions between aldehydes and methyl vinyl ketone(MVK)/acrylate,as well as the aza-MBH reactions between MVK and salicyl N-thiophosphinyl imines.
引文
[1]Chen,X.-M.;Corey.E.J.The Logic of Chemical Synthesis;Wiley:New York,1989
[2]Mahrwald,R.Chem.Rev.1999,99,1095.
[3]F(u|¨)rstner,A.Synthesis 1989,571.
[4]Ziegler,F.E.;Chem.Rev.1988,88,1423.
[5]Olah.G.A.Friedel-Crafts Chemistry[M].Ed:Wiley,New York,1973.
[6]Walborsky,H.M.Acc.Chem.Res.1990,23,286-293.
[7]Oppolzer,W.Angew.Chem.,Int.Ed.Engl.1984,23,876-889.
[8]Maryanoff,B.E.;Reitz,A.B.Chem.Rev.1989,89,863-927.
[9]Mcijcrc,A.;Mcyer,F.E.Angew.Chem.,Int.Ed.1995,33,2379-2411.
[10]Suzuki,A.Metal-catalyzed Cross-coupling Reaction[M]Diderich,F.;Stang,P.J.,Eds,Wiley-VCII Weinhein,Germany,1995,49.
[11]Basavaiah,D.;Rao,A.J.;Satyanarayana,T.Chem.Rev.2003,103,811-891
[12]Morita,K.;Suzuki,Z.;Hirose,H.Bull.Chem.Soc.Jpn.1968,41,2815.
[13]Baylis,A.B.;Hillman,M.E.D.Ger.Offen.2,155,113,172;Chem.Abstr:1972,77,34174q.
[14]Drewes,S.E.J.Chem.Soc.,Perkin Trans.I 1982,2079.
[15]Basavaiah,D.;Rao,A.J.;Hyma,R.S.Tetrahedron 1996,52,8001.
[16]Drowes,S.E.;Roos,G.H.P.Tetrahedron 1988,44,4653.
[17]Ciganek,E.Organic Reactions:Wiley:New York,1997.
[18]Kamimura,A.;Gunjigaket,Y.;Mitsuderat,H.;Yokoyamatt,S.Tetrahedron Lett.1998,39,7323.
[19]Basavaiah,D.;Kumaragurubaran,N.;Sharada,D.S.Tetrahedron Lett.2001,42,85.
[20]Basavaiah,D.;Sharada,D.S.;Kumaragurubaran,N.;Reddy,R.M.J.Org.Chem.2002,67,7135.
[21]Black,P.B.;Dinon,F.;Fratucello,S.;Murphy,P.J.;Nielsen,M.;Williams,H.L. Tetrahedron Lett.1997,38,8561.
[22]Rezgui,F.;Gaied,M.M.E.Tetrahedron Lett.1998,39,5965.
[23]Aggarwal,V.K.;Mereu,A.Chem.Commun.1999,2311.
[24]Kundu,M.K.;Mukherjee,S.B.;Balu,N.;Padmakumar,R.;Bhat,S.V.Synlett 1994,444.
[25]Almeida,W.P.;Coelho,F.Tetrahedron Lett.1998,39,8609.
[26]Rozendaal,E.L.M.;Uoss,B.M.W.;Scbeeren,H.W.Tetrahedron 1993,49,6931.
[27]Li,G.G;Wei,H.X.;Gao,J.J.;Caputo,T.D.Tetrahedron Lett.2000,41,1.
[28]Buskens,P.;Klankermayer,J.;Leitner,W.J.Am.Chem.Soc.2005,127,16762.
[29]Raheem,I.T.;Jacobsen,E.N.Adv.Synth.Catal.2005,347,1701.
[30]Perlmutter,P,;Teo,C.C.Tetrahedron Lett.1984,25,5951.
[31]Yamamoto,K.;Takagi,M.;Tsuji,J.Bull.Chem.Soc.Jpn.1988,61,319.
[32]Takagi,M.;Yamamoto,K.Tetrahedron 1991,47,8869.
[33]Bertenshaw,S.;Kahn,M.Tetrahedron Lett.1989,30,2731.
[34]Xu,Y.-M.;Shi,M.J.Org.Chem.2004,69,417.
[35]Tang,X.;Zhang,B.;He,Z.;Gao,R.;He,Z.Adv.Synth.Catal.2007,349,2007.
[36]Balan,D.;Adolfsson,H.J.Org.Chem.2001,66,6498.
[37]Balan,D.;Adolfsson,H.J.Org.Chem.2002,67,2329.
[38]Kobayashi,S.;Busujima,T.;Nagayama,S.Chem.sEur.J.2000,6,3491.
[39]Aggarwal,V.K.;Mereu,A.;Tarver,G J.;McCague,R.J.Org.Chem.1998,63,7183.
[40]Ribie're,P.;Yadav-Bhatnagar,N.;Martinez,J.;Lamaty,F.QSAR Comb.Sci.2004,23,911.
[41]Ribie're,P.;Enjalbal,C.;Aubagnac,J.-L.;Yadav-Bhatnagar,N.;Martinez,J.;I,amaty,F.J.Comb.Chem.2004,6,464.
[42]Ribie're,P.;Declerck,V.;Martinez,J.;Lamaty,F.Chem.ReV.2006,106,2249.
[43]Declerck,V.;Ribie're,P.;Martinez,J.;Lamaty,F.J.Org.Chem.2004,69,8372.
[44]Wu,Z.;Zhou,G.;Zhou,J.;Guo,W.Synth.Commun.2006,36,2491.
[45]Back,T.G.;Rankic,D.A.;Sorbetti,J.M.;Wulff,J.E.Org.Lett.2005,7,2377.
[46]Sorbetti,J.M.;Clary,K.N.;Rankic,D.A.;Wulff,J.E.;Parvez,M.;Back,T.G.J.Orig.Chem.2007,72,3326.
[47]Clary,K.N.;Back,T.G.Synlett,2007,2995.
[48]IIuang,J.-W.;Shi,M.Adv Synth.Catal.2003,345,953.
[49]Zhao,L.-J.;Song He,H.;Shi,M.;Toy,P.H.J.Comb.Chem.2004,6,680.
[50]Zhao,L.-J.;Kwong,C.K.-W.;Shi,M.;Toy,P.H.Tetrahedron 2005,61,12026.
[51]Richter,H.;Jung,G.Tetrahedron Lett.1998,39,2729.
[52]Cogan,D.A.;Liu,G.;Kim,K.;Backes,B.J.;Ellman,J.A.J.Am.Chem.Soc.1998,120,8011.
[53]Davis,F.A.;Zhang,Y.;emichael,Y.;Fang,T.;Fanelli,D.L.;Zhang,H.J.Orig.Chem.1999,64,1403.
[54]Aggarwal,V.K.;Castro,A.M.M;Mereu,A.;Adams,H.Tetrahedron Lett.2002,43,1577.
[55]Shi,M.;Xu,Y.-M.Tetrahedron:Asymmetry 2002,13,1195.
[56]Shi,M.;Zhao,G.-L.Adv.Synth.Catal.2004,346,1205.
[57]Shi,M.;Zhao,G.-L.Tetrahedron Lett.2002,43,4499.
[581 Weinreb,S.M.;Orr,R.K.Synthesis 2005,1205.
[59]Shi,M.;Zhao,G.-L.Tetrahedron Lett.2002,43,9171.
[60]Xu,X.;Wang,C.;Zhou,Z.;Tang,X.;He,Z.;Tang,C.Eur:J.Org.Chem.2007,4487.
[61]Sergeeva,N.N.;Golubev,A.S.;Burger,K.Synthesis 2001,281.
[621 Liu,X.;Chai,Z.;Zhao,G.;Zhu,S.J.Fluorine Chem.2005,126,1215.
[63]Liu,X.;Zhao,J.;Jin,G;Zhao,G;Zhu,S.;Wang,S.Tetrahedron 2005,61,3841.
[64]Gao,J.;Ma,G.-N.;Li,Q.-J.;Shi,M.Tetrahedron Lett.2006,47,7685.
[65]Myers,E.L.;Butts,C.P.;Aggarwal,V.K.Chem.Commun.2006,4434.
[66]Myers,E.L.;de Vries,J.G.;Aggarwal,V.K.Angew,Chem.,Int.Ed.2007,46,1893.
[67]Shi,Y.-L.;Xu,Y.-M.;Shi,M.AdV.Synth.Catal.2004,346,1220.
[68]Shi,Y.-L.;Shi,M.Tetrahedron 2006,62,461.
[69]Rastogi,N.;Mohan,R.;Panda,D.;Mobin,S.M.;Namboothiri,Ⅰ.N.N.Org.Biomol.Chem.2006,4,3211.
[70]Berthod,M.;Mignani,G;Woodward,G;Lemaire,M.Chem.Rev.2005,105,1801,and references therein.
[71]a) Roth,F.;Gygax,P.;Frator,G Tetrehedron Lett.1992,33,1045.b) Hayase,T.;Shibata,T.;Soai,K.;Wakatsuki,Y.Chem.Commun.1998,1271.c) Li,W.;Zhang,Z.;Xiao,D.;Zhang,X.J.Org.Chem.2000,65,3489.d) Pereira,S.I.;Adrio,J.;Silva,A.M.S.;Carretero,J.C.J.Org.Chem.2005,70,10175.
[72]Shi,M.;Chen,L.-H.;Li,C.-Q,J.Am.Chem.Soc.2005,127,3790.
[73]Shi,M.;Chen,L.-H.Chem.Commun.2003,1310.
[74]Shi,M;Ma,G-N;Gao,J.J.Org.Chem.2007,72,9779.
[75]Shi,M.;Li,C.-Q.Tetrahedron:Asymmetry 2005,16,1385.
[76]Lei,Z.-Y.;Ma,G.-N.;Shi,M.Eur:J.Org.Chem.2005,3817.
[77]Shi,M.;Chen,L.-H.;Teng,W.-D.AdV.Synth.Catal.2005,347,1781.
[78]Liu,Y.-H.;Chen,L.-H.;Shi,M.Adv.Synth.Catal.2006,348,973.
[79]Ito,K.;Nishida,K.;Gotanda,T.Tetrahedron Lett.2007,48,6147.
[80]Qi,M-J.;Ai,T.;Shi,M.;Li,G Tetrahedron 2008,64,1181.
[81]Shi,Y.-L.;Shi,M.AdV.Synth.Catal.2007,349,2129.
[82]Guan,X.-Y.;Jiang,Y.-Q.;Shi,M.Eur.J.Org.Chem.2008,2150.
[83]Liu,Y.-h.;Shi,M.Adv.Synth.Catal.2008,350,122.
[84]Matsui,K.;Takizawa,S.;Sasai,H.Synlett 2006,761.
[85]Garnier,J.M.;Anstiss,C.;Liu,F.Adv.Synth.Catal.2009,351,331.
[86]Iwabuchi,Y.;Nakatani,M.;Yokoyama,N.;IIatakeyama,S.J.Am.Chem.Soc.1999,121,10219.
[87]Shi,M.;Jiang,J.-K.Tetrahedron:Asymmetry 2002,13,1941.
[88]Shi,M.;Xu,Y.-M.;Shi,Y.-L.Chem.-Eur:J.2005,11,1794.
[89]Shi,M.;Xu,Y.-M.Angew.Chem.,Int.Ed.2002,41,4507.
[90]Balan,D.;Adolfsson,H.Tetrahedron Lett.2003,44,2521.
[91]Kawahara,S.;Nakano,A.;Esumi,T.;Iwabuchi,Y.;Hatakeyama,S.Org.Lett.2003,5,3103.
[92]Nakano,A.;Kawahara,S.;Akamatsu,S.;Morokuma,K.;Nakatani,M.;Iwabuchi,Y.;Takahashi,K.;Ishihara,J.;Hatakeyama,S.Tetrahedron 2006,62,381.
[93]Iwabuchi,Y.;Furukawa,M.;Esumi,T.;Hatakeyama,S.Chem.Commun.2001,2030.
[94]Iwabuchi,Y.;Sugihara,T.;Esumi,T.;Hatakeyama,S.Tetrahedron Lett.2001,42,7867.
[95]Matsui,K.;Takizawa,S.;Sasai,H.J.Am.Chem.Soc.2005,127,3680.
[96]Matsui,K.;Tanaka,K.;Horii,A.;Takizawa,S.;Sasai,H.Tetrahedron:Asymmetry 2006,17,578.
[97]Raheem,I.T.;Jacobsen,E.N.Adv.Synth.Catal.2005,347,1701.
[98]Gausepohl,R.;Buskens,P.;Kleinen,J.;Bruckmann,A.;Lehmann,C.W.;Klankermayer,J.;Leitner,W.Angew.Chem..Int.Ed.2006,45,3689.
[99]Shi,M.;Xu,Y.-M.Chem.Commtm.2001,1876.
[100]Shi,M.;Xu,Y.-M.;Zhao,G.-L.;Wu,X.-F.Eur:J.Org.Chem.2002,3666.
[101]He,L.;Jian,T.-Y.;Ye,S.J.Org,.Chem.2007,72,7466.
[102]Shi,M.;Xu,Y.-M.Eur:J.Org.Chem.2002,696.
[103]Shi,M.;Xu,Y.-M.J.Org.Chem.2003,68,4784.
[104]Shi,M.;Zhao,G-L.Adv.Synth.Catal.2004,346,1205.
[105]Zhao,G.-L.;Huang,J.-W.;Shi,M.Org.Lett.2003,5,4737.
[106]Zhao,G.-L.;Shi,M.J.Org.Chem.2005,70,9975.
[107]Qi,M.J.;Shi,M.Tetrahedron,2007,63,10415.
[1]Armstrong,R.W.;Beay,J.-M.;Cheon,S.H.;Christ,W.J.;Fujioka,H.;Ham,W.-H.;Hawkins,L.D.;Jin,H.;Kang,S.H.;Kishi,Y.;Martinelli,M.J.;McWhorter,W.W.;Mizuno,Jr.M.;Nakata,M.;Stutz,A.E.;Talamas,F.X.;Taniguchi,M.;Tino,J.A.;Ueda,K.;Uenishi,J.-i.;White,J.B.;Yonaga,M.J.Am.Chem.Soc.1989,111,7525.
[2]Tieze,L.F.;Beifuss,U.Angew.Chem.,Int.Ed.1993,32,137.
[3]Tieze,L.F.Chem.Rev.1996,96,115.
[4](a) Kaye,P.T.;Nocanda,X.W.J.Chem.Soc.,Perkin Trans.Ⅰ 2000,1331.
(b) Kaye,P.T.;Nocanda,X.W.J.Chem.Soc.,Perkin Trans.Ⅰ 2002,1318.
(c) Kaye,P.T.;Musa,M.A.;Nocanda,X.W.;Robinson,R.S.Org.Biomol.Chem.2003,Ⅰ,1133.
(d) Kaye,P.T.;Musa,M.A.;Nocanda,X.W.Synthesis 2003,531.
(e) Kaye,P.T.;Nocanda,X.W.Synthesis 2001,2389.
[5]Lesch,B.;Br(a|¨)se,S.Angew.Chem.,Int.Ed.2004,43,115.
[6]Shi,Y.-L.;Shi,M.Synlett 2005,2623.
[7](a) Liu,Y.II.;Chen,L.H.;Shi,M.Adv.Synth.Catal.2006,348,973.
(b) Matsui,K.;Tanaka,K.;Horii,A.;Takizawa,S.;Sasai,H.;Tetrahedron:Asymmetry 2006,17,578.
(c) Shi,M.;Chen,L.H.;Pure Appl.Chem.2005,77,2105.
(d) Reddy,M.V.R.;Rudd,M.T.;Ramachandran,P.V.J.Org.Chem.2002,67,5382.
[8]Love,B.E.;Raje,P.S.;Williams,T.C.,Synlett 1994,493.
[9]Pastor,S.D.;Spivack,J.D.;Steinhuebel,L.P.Phosphorus,Sulfur 1987,31,71.
[10]Steinmetz,M.G.;Mayes,R.T.J.Am.Chem.Soc.1985,107,2111
[11]Keglevich,G.;Kerenyi,A;Selke,H.;Ludanyi,K.;Koertvelyesi,T.J.Organomet.Chem.2006,691,5038
[12]CCDC-656007 contains the supplementary crystallographic data for this compound.These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
[13]Xu,Y.M.;Shi,M.J.Org.Chem.2004,69,417.
[1]Zhang,C.M.;Lu,X.Y.J.Org.Chem.1995,60,2906.
[2]Xu,Z.R.;Lu,X.Y.Tetrahedron Lett.1999,40,549.
[3]Xu,Z.R.;Lu,X.Y.Tetrahedron Lett.1997,38,3461.
[4]Zhu,G.X.;Chen,Z.G.;Jiang,Q.Z.;Xiao,D.M.;Cao,P.;Zhang,X.M.J.Am.Chem.Soc.1997,119,3836.
[5](a) Xu,Z.;Lu,X.J.Org.Chem.1995,63,5031.
(b) Kumar,K.;Kapur,A.;Ishar,M.P.S.Org.Lett.2000,2,787.
(c) Ung,A.T.;Schafer,K.;Lindsay,K.B.;Pyne,S.G.;Amornraksa,K.;Wouters,R.;Van der Linden,I.;Biesmans,I.;Lcsage,A.S.J.;Skelton,B.W.;White,A.H.J.Org,.Chem.2002,67,227.
(d) Du,Y.;Lu,X.;Yu,Y.J.Org.Chem.2002,67,8901.
(e) Du,Y.;Lu,X.J.Org.Chem.2003,68,6463.
(f) Hair,V.;Biju,A.T.;Mohanan,K.;Suresh,E.Org.Lett.2006,8,2213.
(g) Lu,X.;Lu,Z.;Zhang,X.Tetrahedron 2006,62,457.
(h) Jean,L.;Marinetti,A.Tetrahedron Lett.2006,47,2141.
(i) Wallace,D.J.;Sidda,R.L.;Reamer,R.A. J.Org.Chem.2007,72,1051.
(j) Henry,C.E.;Kwon,O.Org.Lett.2007,9,3069.
[6](a) Fu,G.C.;Wilson,J.E.Angew.Chem.,Int.Ed.2006,45,1426.
(b) Miller,S.J.;Cowen,B.J.J.Am.Chem.Soc.2007,129,10988.
(c) Jacobsen,E.N.;Fang,Y.Q.J.Am.Chem.Soc.2008,130,5660.
(d) Marinetti,A.;Voituriez,A.;Panossian,A.;Bregeot,N.F.;Retaiileau,P.J.Am.Chem.Soc.2008,130,14030.
(e) Zhu,X.-F.;Henry,C.E.;Kwon,O.Tetrahedron.2005,61,6276.
(f)Wilson,J.E.;Fu,G.C.Angew.Chem.,Int.Ed.2006,45,1426.
(g)Scherer,A.;Gladysz,J.A.Tetrahedron Lett.2006,47,6335.
[7]Wang,J.C.;Krische,M.J.Angew.Chem.,Int.Ed.2003,42,5855.
[8]Shi,Y.L.;Shi,M.Org.Lett.2005,7,3057.
[9](a) Reynaud,J.;Guilet,D.;Terreux,R.;Lussignol,M.;Walchshofer,N.Nat.Prod.Rep.2005,22,504.
(b) Maurya,R.;Yadav,P.P.Nat.Prod.Rep.2005,22,400.
(c) Apers,S.;Vlietinck,A.;Pieters,L.Phytochem.Rev.2003,2,201.
[10]Kuethe,J.T.;Wong,A.;Journet,M.;Davies,I.W.J.Org.Chem.2005,70,3727,and references therein.
[11](a) Bertolini,F.;Crotti,P.;Bussolo,V.D.;Macchia,F.;Pineschi,M.J.Org.Chem.2007,72,7761.
(b) Enders,D.;Niemeier,O.;Straverb,L.Synlett 2006,3399.
(c) Cheung,W.-H.;Sheng,S.-L.;Yu,W.-Y.;Zhou,G.-C.;Che,C.-M.Org.Lett.2003,5,2535.
(d) Saito,H.;Oishi,H.;Kitagaki,S.;Nakamura,S.;Anada,M.;IIashimoto,S.Org.Lett.2002,4,3887.
[12]Birdsall,D.J.;Slawin,A.M.Z.;Woollins,J.D.Polyhedron 2001,20,125.
[13]Shi,M.;Chen,L.-A.;Li,C.-Q.J.Am.Chem.Soc.2005,127,3790.
[14]Meng,X.;Huang,Y.;Chen,R.Chem.-Eur:J.2008,14,6852.
[15]Tran,Y.S.;Kwon,O.Org.Lett.2005,7,4289.
[16]Zhao,G.-L.;Shi,M.Org.Biomol.Chem.2005,3,3686.
[17]Trost,B.M.;Li,C.-J.J.Am.Chem.Soc.1994,116,10819.
[1]Zhang,C.M.;Lu,X.Y.J.Org.Chem.1995,60,2906.
[2](a) Tran,Y.S.;Kwon,O.J.Am.Chem.Soc.2007,129,12632.
(b) Castellano,S.;Fiji,H.D.G.;Kinderman,S.S.;Watanabe,M.;de Leon,P.;Tamanoi,F.;Kwon,O.J.Am.Chem.Soc.2007,129,5843.
(c) Wurz,R.P.;Fu,G.C.J.Am.Chem.Soc.2005,127,12234.
(d) Zhu,X.-F.;Lan,J.;Kwon,O.J.Am.Chem.Soc.2003,125,4716.
(e) Zh,X.-F.;Schaffner,A.-P.;Li,R.C.;Kwon,O,Org.Lett.2005,7,2977.
[3]Tran,Y.S.;Kwon,O.Org.Lett.2005,7,4289.
[4](a) Lu,Z.;Zheng,S.;Zhang,X.;Lu,X.Org.Lett.2008,10,3267.
(b) Zhu,X.-F.;Henry,C.E.;Wang,J.;Dudding,T.;Kwon,O.Org.Lett.2005,7,1387.
[5](a) Liang,Y.;Liu,S.;Yu,Z.X.Synlett.2009,905.
(b) Guo,H.C.;Xu,Q.H.;Kwon,O.J.Am.Chem.Soc.2009,ASAP,DOI:10.1021/ja8097349.
[6]Meng,X.;Huang,Y.;Chen,R.Org.Lett.2009,11,137.
[7](a) Kleschick,W.A.;Heathcock,C.H.J.Org.Chem.1978,43,1256.
(b) Minami,T.;Suganuma,H.;Agawa,T.Chem.Lett.1978,285.
(c) Wang,Q.;Finn,M.G.Org.Lett.2000,2,4063.
(d) Chang,S.;Grubbs,R.H.J.Org.Chem.1998,63,864.
(e) Gopal,D.;Rajagopalan,K.Tetrahedron Lett.1987,28,5327.
(f) Ellis,G.P.Chromenes,Chromanones,and Chromanones,and Chromones.In The Chemisry of Heterocyclic Compounds;Wiley:New York,1977;Vol.31,pp 11-139.
(g) Hepworth,J.In ComprehensiVe Heterocyclic Chemistry;Katrizky,A.R.,Rees,C.W.,Eds.;Pergamon;Oxford,UK,1984;Vol.3,pp 737-883.
(h) Bowers,W.S.;Ohta,T.;Cleere,J.S.;Marsella,P.A.Science 1976,193,542.
(i)Nicolaou,K.C.;Pfefferkorn,J.A.;Roecker,A.J.;Cao,G.-Q.;Barluenga,S.;Mitchell,H.J.J.Am.Chem.Soc.2000,122,9939.
(j) Nicolaou,K.C.;Pfefferkorn,J.A.;Mitchell,H.J.;Roecker,A.J.;Barluenga,S.;Cao,G.-Q.;Affleck,R.L.;Lillig,J.E.J.Am.Chem.Soc.2000,122,9954.
(k) Nicolaou,K.C.;Pfefferkorn,J.A.;Barluenga,S.;Mitchell,H.J.;Roecker,A.J.;Cao,G.-Q.J.Am.Chem.Soc.2000,122,9968.
[8](a) Lesch,B.;Brase,S.Angew.Chem.,Int.Ed.2004,43,115.
(b) Lee,K.Y.;Kim,J.M.;Kim,J.N.Bull.Korean Chem.Soc.2003,24,17.
(c) Kaya,P.T.;Nocanda,X.W.J.Chem.Soc.,Perkin Trans.1 2000,1331.
(d) DeBoer,C.D.J.Org.Chem.1974,39,2426.
(e) Korotaev,V.Yu.;Kutyashev,I.B.;Sosnovskikh,V.Ya.Heteroatom.Chem.2005,16,492.
[9](a) Kaya,P.T.;Robinson,R.S.Synth.Commun.1996,26,2085.
(b) Kaya,P.T.;Musa,M.A.;Nocanda,X.W.Synthesis 2003,531.
(c) Kaya,P.T.;Musa,M.A.;Nocanda,X.W.;Robinson,R.S.Org.Biomol.Chem.2003,1,1133.
[10](a) Yan,M.-C.;Jang,Y.-J.;Yao,C.F.Tetrahedron Lett.2001,42,2717.
(b) Yao,C.F.;Jang,Y.-J.;Yan,M.-C.Tetrahedron Lett.2003,44,3813.
(c) Nyerges,M.;Viranyi,A.;Marth,G.;Dancso,A.;Balasko,G.;oke,L.Synlett 2004,2761.
[11](a) Yamaguchi,S.;Saitoh,T.;Kamiumezawa,M.;Enomoto,H.;Kawase,Y.J.Heterocycl.Chem.1992,29,755.
(b) Kawase,Y.;Yamaguchi,S.;Horita,H.Bull.Chem.Soc.Jpn.1982,55,1153.
(c) Sharma,K.K.;Krupadanam,G.L.D.Synth.Commun.2002,32,1557.
[12](a) Zhao,G.-L.;Shi,Y.-L.;Shi,M.Org.Lett.2005,7,4527.
(b) Dai,L.-Z.;Shi,Y.-L.;Zhao,G.-L.;Shi,M.Chem.-Eur.J.2007,13,3701.
[13]Franklin,N.C.Angew.Chem.,Int.Ed.1965,4,774.
[14](a) Liang,Y.;Liu,S.;Xia,Y.;Li,Y.;Yu,Z.-X.Chem.-Eur:J.2008,14,4361.
(b) Xia,Y.;Liang,Y.;Chen,Y.;Wang,M.;Jiao,L.;Huang,F.;Liu,S.;Li,Y.;Yu,Z.-X.J.Am.Chem.Soc.2007,129,3470.
[1]Morita,K.;Suzuki,Z.;IIirose,H.Bull.Chem.Soc.Jpn.1968,41,2815.
[2]B aylis,A.B.;Hillman,M.E.D.;German Patent 2155113,1972.
[3]Dadwal,M.;Mohan,R.;Panda,D,;Mobin,S.M.;Namboothiri,I.N.N.Chem.Commun.2006,338.
[4]Hong,W.P.;Lee,K.J.Synthesis 2006,963.
[5]Trost,B.M.;Machacek,M.H.;Tsui,H.C.J.Am.Chem.Soc.2005,127,7014.
[6](a) Jenner,G.High-Pressure Res.1999,16,243-252.
(b) Kun,M.K.;Mukherjee,S.B.;Balu,N.;Padmakumar,R.;Bhat,S.V.Synlett 1994,444-446.
[7](a) aggarwal,V.K.;Tarver,G.J.;McCague,R.Chem.Commun.1996,2713.
(b) Rafel,S.;Leahy,J.W.J.Org.Chem.1997,62,1521.
(d) Aggarwal,V.K.;Mereu,A.;Tarver,G.J.; McCague, R. J. Org. Chem. 1998, 63, 7183. (e) Aggarwal, V. K.; Mereu, A. Chem. Commun.1999, 2311. (f) Basavaiah, D.; Kumaragurabaran, N. Tetrahedron Lett. 2001, 42, 477.
[8] Shi, M. ; Liu, Y. H. Org. Biomol. Chem. 2006, 4, 1468.
[9] Brand, M; Drewes, S. E.; Loizou, G.; Roos, G. H. P. Synth. Commun. 1987, 17, 795.
[10] Shi, M.; Li, C. Q.; Jiang, J. K. Chem. Commun. 2001, 833.
[11] Iwama, T.; Kinoshita, H; Kataoka, T. Tetrahedron Lett. 1999, 40, 3741.
[12] Shi, M.; Jiang, J. K.; Li, C. Q. Tetrahedron Lett. 2001, 43, 127.
[13] Kataoka, T.; Iwama, T; Tsujiyama, S. Chem. Commun. 1998, 197.
[14] Basavaiah, D.; Krishnamacharyulu, M.; Rao, J. Synth. Commun. 2000, 30, 2061.
[15] Yu, C. Z.; Liu, B.; Hu, L. Q. J. Org. Chem. 2001, 66, 5413.
[16] Ameer, F.; Drewes, S. E.; Freese, S.; Kaye, P. T. Synth. Commun. 1988, 18, 495.
[17] Rosa, J. N.; Afonso, C. A. M.; Santos, A. G Tetrahedron 2001, 57, 4189.
[18] Mi, X. L.; Luo, S. Z.; Xu, H; Zhang, L.; Cheng, J. P. Tetrahedron 2006, 62, 2537.
[19] Balan, D.; Adolfsson, H. J. Org. Chem. 2001, 66, 6498.
[20] Kaye, P. T.; Nocanda, X. W. J. Chem. Soc., Perkin Trans. 1 2000, 1331.
[2]Mahrwald,R.Chem.Rev.1999,99,1095.
[3]F(u|¨)rstner,A.Synthesis 1989,571.
[4]Ziegler,F.E.;Chem.Rev.1988,88,1423.
[5]Olah.G.A.Friedel-Crafts Chemistry[M].Ed:Wiley,New York,1973.
[6]Walborsky,H.M.Acc.Chem.Res.1990,23,286-293.
[7]Oppolzer,W.Angew.Chem.,Int.Ed.Engl.1984,23,876-889.
[8]Maryanoff,B.E.;Reitz,A.B.Chem.Rev.1989,89,863-927.
[9]Mcijcrc,A.;Mcyer,F.E.Angew.Chem.,Int.Ed.1995,33,2379-2411.
[10]Suzuki,A.Metal-catalyzed Cross-coupling Reaction[M]Diderich,F.;Stang,P.J.,Eds,Wiley-VCII Weinhein,Germany,1995,49.
[11]Basavaiah,D.;Rao,A.J.;Satyanarayana,T.Chem.Rev.2003,103,811-891
[12]Morita,K.;Suzuki,Z.;Hirose,H.Bull.Chem.Soc.Jpn.1968,41,2815.
[13]Baylis,A.B.;Hillman,M.E.D.Ger.Offen.2,155,113,172;Chem.Abstr:1972,77,34174q.
[14]Drewes,S.E.J.Chem.Soc.,Perkin Trans.I 1982,2079.
[15]Basavaiah,D.;Rao,A.J.;Hyma,R.S.Tetrahedron 1996,52,8001.
[16]Drowes,S.E.;Roos,G.H.P.Tetrahedron 1988,44,4653.
[17]Ciganek,E.Organic Reactions:Wiley:New York,1997.
[18]Kamimura,A.;Gunjigaket,Y.;Mitsuderat,H.;Yokoyamatt,S.Tetrahedron Lett.1998,39,7323.
[19]Basavaiah,D.;Kumaragurubaran,N.;Sharada,D.S.Tetrahedron Lett.2001,42,85.
[20]Basavaiah,D.;Sharada,D.S.;Kumaragurubaran,N.;Reddy,R.M.J.Org.Chem.2002,67,7135.
[21]Black,P.B.;Dinon,F.;Fratucello,S.;Murphy,P.J.;Nielsen,M.;Williams,H.L. Tetrahedron Lett.1997,38,8561.
[22]Rezgui,F.;Gaied,M.M.E.Tetrahedron Lett.1998,39,5965.
[23]Aggarwal,V.K.;Mereu,A.Chem.Commun.1999,2311.
[24]Kundu,M.K.;Mukherjee,S.B.;Balu,N.;Padmakumar,R.;Bhat,S.V.Synlett 1994,444.
[25]Almeida,W.P.;Coelho,F.Tetrahedron Lett.1998,39,8609.
[26]Rozendaal,E.L.M.;Uoss,B.M.W.;Scbeeren,H.W.Tetrahedron 1993,49,6931.
[27]Li,G.G;Wei,H.X.;Gao,J.J.;Caputo,T.D.Tetrahedron Lett.2000,41,1.
[28]Buskens,P.;Klankermayer,J.;Leitner,W.J.Am.Chem.Soc.2005,127,16762.
[29]Raheem,I.T.;Jacobsen,E.N.Adv.Synth.Catal.2005,347,1701.
[30]Perlmutter,P,;Teo,C.C.Tetrahedron Lett.1984,25,5951.
[31]Yamamoto,K.;Takagi,M.;Tsuji,J.Bull.Chem.Soc.Jpn.1988,61,319.
[32]Takagi,M.;Yamamoto,K.Tetrahedron 1991,47,8869.
[33]Bertenshaw,S.;Kahn,M.Tetrahedron Lett.1989,30,2731.
[34]Xu,Y.-M.;Shi,M.J.Org.Chem.2004,69,417.
[35]Tang,X.;Zhang,B.;He,Z.;Gao,R.;He,Z.Adv.Synth.Catal.2007,349,2007.
[36]Balan,D.;Adolfsson,H.J.Org.Chem.2001,66,6498.
[37]Balan,D.;Adolfsson,H.J.Org.Chem.2002,67,2329.
[38]Kobayashi,S.;Busujima,T.;Nagayama,S.Chem.sEur.J.2000,6,3491.
[39]Aggarwal,V.K.;Mereu,A.;Tarver,G J.;McCague,R.J.Org.Chem.1998,63,7183.
[40]Ribie're,P.;Yadav-Bhatnagar,N.;Martinez,J.;Lamaty,F.QSAR Comb.Sci.2004,23,911.
[41]Ribie're,P.;Enjalbal,C.;Aubagnac,J.-L.;Yadav-Bhatnagar,N.;Martinez,J.;I,amaty,F.J.Comb.Chem.2004,6,464.
[42]Ribie're,P.;Declerck,V.;Martinez,J.;Lamaty,F.Chem.ReV.2006,106,2249.
[43]Declerck,V.;Ribie're,P.;Martinez,J.;Lamaty,F.J.Org.Chem.2004,69,8372.
[44]Wu,Z.;Zhou,G.;Zhou,J.;Guo,W.Synth.Commun.2006,36,2491.
[45]Back,T.G.;Rankic,D.A.;Sorbetti,J.M.;Wulff,J.E.Org.Lett.2005,7,2377.
[46]Sorbetti,J.M.;Clary,K.N.;Rankic,D.A.;Wulff,J.E.;Parvez,M.;Back,T.G.J.Orig.Chem.2007,72,3326.
[47]Clary,K.N.;Back,T.G.Synlett,2007,2995.
[48]IIuang,J.-W.;Shi,M.Adv Synth.Catal.2003,345,953.
[49]Zhao,L.-J.;Song He,H.;Shi,M.;Toy,P.H.J.Comb.Chem.2004,6,680.
[50]Zhao,L.-J.;Kwong,C.K.-W.;Shi,M.;Toy,P.H.Tetrahedron 2005,61,12026.
[51]Richter,H.;Jung,G.Tetrahedron Lett.1998,39,2729.
[52]Cogan,D.A.;Liu,G.;Kim,K.;Backes,B.J.;Ellman,J.A.J.Am.Chem.Soc.1998,120,8011.
[53]Davis,F.A.;Zhang,Y.;emichael,Y.;Fang,T.;Fanelli,D.L.;Zhang,H.J.Orig.Chem.1999,64,1403.
[54]Aggarwal,V.K.;Castro,A.M.M;Mereu,A.;Adams,H.Tetrahedron Lett.2002,43,1577.
[55]Shi,M.;Xu,Y.-M.Tetrahedron:Asymmetry 2002,13,1195.
[56]Shi,M.;Zhao,G.-L.Adv.Synth.Catal.2004,346,1205.
[57]Shi,M.;Zhao,G.-L.Tetrahedron Lett.2002,43,4499.
[581 Weinreb,S.M.;Orr,R.K.Synthesis 2005,1205.
[59]Shi,M.;Zhao,G.-L.Tetrahedron Lett.2002,43,9171.
[60]Xu,X.;Wang,C.;Zhou,Z.;Tang,X.;He,Z.;Tang,C.Eur:J.Org.Chem.2007,4487.
[61]Sergeeva,N.N.;Golubev,A.S.;Burger,K.Synthesis 2001,281.
[621 Liu,X.;Chai,Z.;Zhao,G.;Zhu,S.J.Fluorine Chem.2005,126,1215.
[63]Liu,X.;Zhao,J.;Jin,G;Zhao,G;Zhu,S.;Wang,S.Tetrahedron 2005,61,3841.
[64]Gao,J.;Ma,G.-N.;Li,Q.-J.;Shi,M.Tetrahedron Lett.2006,47,7685.
[65]Myers,E.L.;Butts,C.P.;Aggarwal,V.K.Chem.Commun.2006,4434.
[66]Myers,E.L.;de Vries,J.G.;Aggarwal,V.K.Angew,Chem.,Int.Ed.2007,46,1893.
[67]Shi,Y.-L.;Xu,Y.-M.;Shi,M.AdV.Synth.Catal.2004,346,1220.
[68]Shi,Y.-L.;Shi,M.Tetrahedron 2006,62,461.
[69]Rastogi,N.;Mohan,R.;Panda,D.;Mobin,S.M.;Namboothiri,Ⅰ.N.N.Org.Biomol.Chem.2006,4,3211.
[70]Berthod,M.;Mignani,G;Woodward,G;Lemaire,M.Chem.Rev.2005,105,1801,and references therein.
[71]a) Roth,F.;Gygax,P.;Frator,G Tetrehedron Lett.1992,33,1045.b) Hayase,T.;Shibata,T.;Soai,K.;Wakatsuki,Y.Chem.Commun.1998,1271.c) Li,W.;Zhang,Z.;Xiao,D.;Zhang,X.J.Org.Chem.2000,65,3489.d) Pereira,S.I.;Adrio,J.;Silva,A.M.S.;Carretero,J.C.J.Org.Chem.2005,70,10175.
[72]Shi,M.;Chen,L.-H.;Li,C.-Q,J.Am.Chem.Soc.2005,127,3790.
[73]Shi,M.;Chen,L.-H.Chem.Commun.2003,1310.
[74]Shi,M;Ma,G-N;Gao,J.J.Org.Chem.2007,72,9779.
[75]Shi,M.;Li,C.-Q.Tetrahedron:Asymmetry 2005,16,1385.
[76]Lei,Z.-Y.;Ma,G.-N.;Shi,M.Eur:J.Org.Chem.2005,3817.
[77]Shi,M.;Chen,L.-H.;Teng,W.-D.AdV.Synth.Catal.2005,347,1781.
[78]Liu,Y.-H.;Chen,L.-H.;Shi,M.Adv.Synth.Catal.2006,348,973.
[79]Ito,K.;Nishida,K.;Gotanda,T.Tetrahedron Lett.2007,48,6147.
[80]Qi,M-J.;Ai,T.;Shi,M.;Li,G Tetrahedron 2008,64,1181.
[81]Shi,Y.-L.;Shi,M.AdV.Synth.Catal.2007,349,2129.
[82]Guan,X.-Y.;Jiang,Y.-Q.;Shi,M.Eur.J.Org.Chem.2008,2150.
[83]Liu,Y.-h.;Shi,M.Adv.Synth.Catal.2008,350,122.
[84]Matsui,K.;Takizawa,S.;Sasai,H.Synlett 2006,761.
[85]Garnier,J.M.;Anstiss,C.;Liu,F.Adv.Synth.Catal.2009,351,331.
[86]Iwabuchi,Y.;Nakatani,M.;Yokoyama,N.;IIatakeyama,S.J.Am.Chem.Soc.1999,121,10219.
[87]Shi,M.;Jiang,J.-K.Tetrahedron:Asymmetry 2002,13,1941.
[88]Shi,M.;Xu,Y.-M.;Shi,Y.-L.Chem.-Eur:J.2005,11,1794.
[89]Shi,M.;Xu,Y.-M.Angew.Chem.,Int.Ed.2002,41,4507.
[90]Balan,D.;Adolfsson,H.Tetrahedron Lett.2003,44,2521.
[91]Kawahara,S.;Nakano,A.;Esumi,T.;Iwabuchi,Y.;Hatakeyama,S.Org.Lett.2003,5,3103.
[92]Nakano,A.;Kawahara,S.;Akamatsu,S.;Morokuma,K.;Nakatani,M.;Iwabuchi,Y.;Takahashi,K.;Ishihara,J.;Hatakeyama,S.Tetrahedron 2006,62,381.
[93]Iwabuchi,Y.;Furukawa,M.;Esumi,T.;Hatakeyama,S.Chem.Commun.2001,2030.
[94]Iwabuchi,Y.;Sugihara,T.;Esumi,T.;Hatakeyama,S.Tetrahedron Lett.2001,42,7867.
[95]Matsui,K.;Takizawa,S.;Sasai,H.J.Am.Chem.Soc.2005,127,3680.
[96]Matsui,K.;Tanaka,K.;Horii,A.;Takizawa,S.;Sasai,H.Tetrahedron:Asymmetry 2006,17,578.
[97]Raheem,I.T.;Jacobsen,E.N.Adv.Synth.Catal.2005,347,1701.
[98]Gausepohl,R.;Buskens,P.;Kleinen,J.;Bruckmann,A.;Lehmann,C.W.;Klankermayer,J.;Leitner,W.Angew.Chem..Int.Ed.2006,45,3689.
[99]Shi,M.;Xu,Y.-M.Chem.Commtm.2001,1876.
[100]Shi,M.;Xu,Y.-M.;Zhao,G.-L.;Wu,X.-F.Eur:J.Org.Chem.2002,3666.
[101]He,L.;Jian,T.-Y.;Ye,S.J.Org,.Chem.2007,72,7466.
[102]Shi,M.;Xu,Y.-M.Eur:J.Org.Chem.2002,696.
[103]Shi,M.;Xu,Y.-M.J.Org.Chem.2003,68,4784.
[104]Shi,M.;Zhao,G-L.Adv.Synth.Catal.2004,346,1205.
[105]Zhao,G.-L.;Huang,J.-W.;Shi,M.Org.Lett.2003,5,4737.
[106]Zhao,G.-L.;Shi,M.J.Org.Chem.2005,70,9975.
[107]Qi,M.J.;Shi,M.Tetrahedron,2007,63,10415.
[1]Armstrong,R.W.;Beay,J.-M.;Cheon,S.H.;Christ,W.J.;Fujioka,H.;Ham,W.-H.;Hawkins,L.D.;Jin,H.;Kang,S.H.;Kishi,Y.;Martinelli,M.J.;McWhorter,W.W.;Mizuno,Jr.M.;Nakata,M.;Stutz,A.E.;Talamas,F.X.;Taniguchi,M.;Tino,J.A.;Ueda,K.;Uenishi,J.-i.;White,J.B.;Yonaga,M.J.Am.Chem.Soc.1989,111,7525.
[2]Tieze,L.F.;Beifuss,U.Angew.Chem.,Int.Ed.1993,32,137.
[3]Tieze,L.F.Chem.Rev.1996,96,115.
[4](a) Kaye,P.T.;Nocanda,X.W.J.Chem.Soc.,Perkin Trans.Ⅰ 2000,1331.
(b) Kaye,P.T.;Nocanda,X.W.J.Chem.Soc.,Perkin Trans.Ⅰ 2002,1318.
(c) Kaye,P.T.;Musa,M.A.;Nocanda,X.W.;Robinson,R.S.Org.Biomol.Chem.2003,Ⅰ,1133.
(d) Kaye,P.T.;Musa,M.A.;Nocanda,X.W.Synthesis 2003,531.
(e) Kaye,P.T.;Nocanda,X.W.Synthesis 2001,2389.
[5]Lesch,B.;Br(a|¨)se,S.Angew.Chem.,Int.Ed.2004,43,115.
[6]Shi,Y.-L.;Shi,M.Synlett 2005,2623.
[7](a) Liu,Y.II.;Chen,L.H.;Shi,M.Adv.Synth.Catal.2006,348,973.
(b) Matsui,K.;Tanaka,K.;Horii,A.;Takizawa,S.;Sasai,H.;Tetrahedron:Asymmetry 2006,17,578.
(c) Shi,M.;Chen,L.H.;Pure Appl.Chem.2005,77,2105.
(d) Reddy,M.V.R.;Rudd,M.T.;Ramachandran,P.V.J.Org.Chem.2002,67,5382.
[8]Love,B.E.;Raje,P.S.;Williams,T.C.,Synlett 1994,493.
[9]Pastor,S.D.;Spivack,J.D.;Steinhuebel,L.P.Phosphorus,Sulfur 1987,31,71.
[10]Steinmetz,M.G.;Mayes,R.T.J.Am.Chem.Soc.1985,107,2111
[11]Keglevich,G.;Kerenyi,A;Selke,H.;Ludanyi,K.;Koertvelyesi,T.J.Organomet.Chem.2006,691,5038
[12]CCDC-656007 contains the supplementary crystallographic data for this compound.These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
[13]Xu,Y.M.;Shi,M.J.Org.Chem.2004,69,417.
[1]Zhang,C.M.;Lu,X.Y.J.Org.Chem.1995,60,2906.
[2]Xu,Z.R.;Lu,X.Y.Tetrahedron Lett.1999,40,549.
[3]Xu,Z.R.;Lu,X.Y.Tetrahedron Lett.1997,38,3461.
[4]Zhu,G.X.;Chen,Z.G.;Jiang,Q.Z.;Xiao,D.M.;Cao,P.;Zhang,X.M.J.Am.Chem.Soc.1997,119,3836.
[5](a) Xu,Z.;Lu,X.J.Org.Chem.1995,63,5031.
(b) Kumar,K.;Kapur,A.;Ishar,M.P.S.Org.Lett.2000,2,787.
(c) Ung,A.T.;Schafer,K.;Lindsay,K.B.;Pyne,S.G.;Amornraksa,K.;Wouters,R.;Van der Linden,I.;Biesmans,I.;Lcsage,A.S.J.;Skelton,B.W.;White,A.H.J.Org,.Chem.2002,67,227.
(d) Du,Y.;Lu,X.;Yu,Y.J.Org.Chem.2002,67,8901.
(e) Du,Y.;Lu,X.J.Org.Chem.2003,68,6463.
(f) Hair,V.;Biju,A.T.;Mohanan,K.;Suresh,E.Org.Lett.2006,8,2213.
(g) Lu,X.;Lu,Z.;Zhang,X.Tetrahedron 2006,62,457.
(h) Jean,L.;Marinetti,A.Tetrahedron Lett.2006,47,2141.
(i) Wallace,D.J.;Sidda,R.L.;Reamer,R.A. J.Org.Chem.2007,72,1051.
(j) Henry,C.E.;Kwon,O.Org.Lett.2007,9,3069.
[6](a) Fu,G.C.;Wilson,J.E.Angew.Chem.,Int.Ed.2006,45,1426.
(b) Miller,S.J.;Cowen,B.J.J.Am.Chem.Soc.2007,129,10988.
(c) Jacobsen,E.N.;Fang,Y.Q.J.Am.Chem.Soc.2008,130,5660.
(d) Marinetti,A.;Voituriez,A.;Panossian,A.;Bregeot,N.F.;Retaiileau,P.J.Am.Chem.Soc.2008,130,14030.
(e) Zhu,X.-F.;Henry,C.E.;Kwon,O.Tetrahedron.2005,61,6276.
(f)Wilson,J.E.;Fu,G.C.Angew.Chem.,Int.Ed.2006,45,1426.
(g)Scherer,A.;Gladysz,J.A.Tetrahedron Lett.2006,47,6335.
[7]Wang,J.C.;Krische,M.J.Angew.Chem.,Int.Ed.2003,42,5855.
[8]Shi,Y.L.;Shi,M.Org.Lett.2005,7,3057.
[9](a) Reynaud,J.;Guilet,D.;Terreux,R.;Lussignol,M.;Walchshofer,N.Nat.Prod.Rep.2005,22,504.
(b) Maurya,R.;Yadav,P.P.Nat.Prod.Rep.2005,22,400.
(c) Apers,S.;Vlietinck,A.;Pieters,L.Phytochem.Rev.2003,2,201.
[10]Kuethe,J.T.;Wong,A.;Journet,M.;Davies,I.W.J.Org.Chem.2005,70,3727,and references therein.
[11](a) Bertolini,F.;Crotti,P.;Bussolo,V.D.;Macchia,F.;Pineschi,M.J.Org.Chem.2007,72,7761.
(b) Enders,D.;Niemeier,O.;Straverb,L.Synlett 2006,3399.
(c) Cheung,W.-H.;Sheng,S.-L.;Yu,W.-Y.;Zhou,G.-C.;Che,C.-M.Org.Lett.2003,5,2535.
(d) Saito,H.;Oishi,H.;Kitagaki,S.;Nakamura,S.;Anada,M.;IIashimoto,S.Org.Lett.2002,4,3887.
[12]Birdsall,D.J.;Slawin,A.M.Z.;Woollins,J.D.Polyhedron 2001,20,125.
[13]Shi,M.;Chen,L.-A.;Li,C.-Q.J.Am.Chem.Soc.2005,127,3790.
[14]Meng,X.;Huang,Y.;Chen,R.Chem.-Eur:J.2008,14,6852.
[15]Tran,Y.S.;Kwon,O.Org.Lett.2005,7,4289.
[16]Zhao,G.-L.;Shi,M.Org.Biomol.Chem.2005,3,3686.
[17]Trost,B.M.;Li,C.-J.J.Am.Chem.Soc.1994,116,10819.
[1]Zhang,C.M.;Lu,X.Y.J.Org.Chem.1995,60,2906.
[2](a) Tran,Y.S.;Kwon,O.J.Am.Chem.Soc.2007,129,12632.
(b) Castellano,S.;Fiji,H.D.G.;Kinderman,S.S.;Watanabe,M.;de Leon,P.;Tamanoi,F.;Kwon,O.J.Am.Chem.Soc.2007,129,5843.
(c) Wurz,R.P.;Fu,G.C.J.Am.Chem.Soc.2005,127,12234.
(d) Zhu,X.-F.;Lan,J.;Kwon,O.J.Am.Chem.Soc.2003,125,4716.
(e) Zh,X.-F.;Schaffner,A.-P.;Li,R.C.;Kwon,O,Org.Lett.2005,7,2977.
[3]Tran,Y.S.;Kwon,O.Org.Lett.2005,7,4289.
[4](a) Lu,Z.;Zheng,S.;Zhang,X.;Lu,X.Org.Lett.2008,10,3267.
(b) Zhu,X.-F.;Henry,C.E.;Wang,J.;Dudding,T.;Kwon,O.Org.Lett.2005,7,1387.
[5](a) Liang,Y.;Liu,S.;Yu,Z.X.Synlett.2009,905.
(b) Guo,H.C.;Xu,Q.H.;Kwon,O.J.Am.Chem.Soc.2009,ASAP,DOI:10.1021/ja8097349.
[6]Meng,X.;Huang,Y.;Chen,R.Org.Lett.2009,11,137.
[7](a) Kleschick,W.A.;Heathcock,C.H.J.Org.Chem.1978,43,1256.
(b) Minami,T.;Suganuma,H.;Agawa,T.Chem.Lett.1978,285.
(c) Wang,Q.;Finn,M.G.Org.Lett.2000,2,4063.
(d) Chang,S.;Grubbs,R.H.J.Org.Chem.1998,63,864.
(e) Gopal,D.;Rajagopalan,K.Tetrahedron Lett.1987,28,5327.
(f) Ellis,G.P.Chromenes,Chromanones,and Chromanones,and Chromones.In The Chemisry of Heterocyclic Compounds;Wiley:New York,1977;Vol.31,pp 11-139.
(g) Hepworth,J.In ComprehensiVe Heterocyclic Chemistry;Katrizky,A.R.,Rees,C.W.,Eds.;Pergamon;Oxford,UK,1984;Vol.3,pp 737-883.
(h) Bowers,W.S.;Ohta,T.;Cleere,J.S.;Marsella,P.A.Science 1976,193,542.
(i)Nicolaou,K.C.;Pfefferkorn,J.A.;Roecker,A.J.;Cao,G.-Q.;Barluenga,S.;Mitchell,H.J.J.Am.Chem.Soc.2000,122,9939.
(j) Nicolaou,K.C.;Pfefferkorn,J.A.;Mitchell,H.J.;Roecker,A.J.;Barluenga,S.;Cao,G.-Q.;Affleck,R.L.;Lillig,J.E.J.Am.Chem.Soc.2000,122,9954.
(k) Nicolaou,K.C.;Pfefferkorn,J.A.;Barluenga,S.;Mitchell,H.J.;Roecker,A.J.;Cao,G.-Q.J.Am.Chem.Soc.2000,122,9968.
[8](a) Lesch,B.;Brase,S.Angew.Chem.,Int.Ed.2004,43,115.
(b) Lee,K.Y.;Kim,J.M.;Kim,J.N.Bull.Korean Chem.Soc.2003,24,17.
(c) Kaya,P.T.;Nocanda,X.W.J.Chem.Soc.,Perkin Trans.1 2000,1331.
(d) DeBoer,C.D.J.Org.Chem.1974,39,2426.
(e) Korotaev,V.Yu.;Kutyashev,I.B.;Sosnovskikh,V.Ya.Heteroatom.Chem.2005,16,492.
[9](a) Kaya,P.T.;Robinson,R.S.Synth.Commun.1996,26,2085.
(b) Kaya,P.T.;Musa,M.A.;Nocanda,X.W.Synthesis 2003,531.
(c) Kaya,P.T.;Musa,M.A.;Nocanda,X.W.;Robinson,R.S.Org.Biomol.Chem.2003,1,1133.
[10](a) Yan,M.-C.;Jang,Y.-J.;Yao,C.F.Tetrahedron Lett.2001,42,2717.
(b) Yao,C.F.;Jang,Y.-J.;Yan,M.-C.Tetrahedron Lett.2003,44,3813.
(c) Nyerges,M.;Viranyi,A.;Marth,G.;Dancso,A.;Balasko,G.;oke,L.Synlett 2004,2761.
[11](a) Yamaguchi,S.;Saitoh,T.;Kamiumezawa,M.;Enomoto,H.;Kawase,Y.J.Heterocycl.Chem.1992,29,755.
(b) Kawase,Y.;Yamaguchi,S.;Horita,H.Bull.Chem.Soc.Jpn.1982,55,1153.
(c) Sharma,K.K.;Krupadanam,G.L.D.Synth.Commun.2002,32,1557.
[12](a) Zhao,G.-L.;Shi,Y.-L.;Shi,M.Org.Lett.2005,7,4527.
(b) Dai,L.-Z.;Shi,Y.-L.;Zhao,G.-L.;Shi,M.Chem.-Eur.J.2007,13,3701.
[13]Franklin,N.C.Angew.Chem.,Int.Ed.1965,4,774.
[14](a) Liang,Y.;Liu,S.;Xia,Y.;Li,Y.;Yu,Z.-X.Chem.-Eur:J.2008,14,4361.
(b) Xia,Y.;Liang,Y.;Chen,Y.;Wang,M.;Jiao,L.;Huang,F.;Liu,S.;Li,Y.;Yu,Z.-X.J.Am.Chem.Soc.2007,129,3470.
[1]Morita,K.;Suzuki,Z.;IIirose,H.Bull.Chem.Soc.Jpn.1968,41,2815.
[2]B aylis,A.B.;Hillman,M.E.D.;German Patent 2155113,1972.
[3]Dadwal,M.;Mohan,R.;Panda,D,;Mobin,S.M.;Namboothiri,I.N.N.Chem.Commun.2006,338.
[4]Hong,W.P.;Lee,K.J.Synthesis 2006,963.
[5]Trost,B.M.;Machacek,M.H.;Tsui,H.C.J.Am.Chem.Soc.2005,127,7014.
[6](a) Jenner,G.High-Pressure Res.1999,16,243-252.
(b) Kun,M.K.;Mukherjee,S.B.;Balu,N.;Padmakumar,R.;Bhat,S.V.Synlett 1994,444-446.
[7](a) aggarwal,V.K.;Tarver,G.J.;McCague,R.Chem.Commun.1996,2713.
(b) Rafel,S.;Leahy,J.W.J.Org.Chem.1997,62,1521.
(d) Aggarwal,V.K.;Mereu,A.;Tarver,G.J.; McCague, R. J. Org. Chem. 1998, 63, 7183. (e) Aggarwal, V. K.; Mereu, A. Chem. Commun.1999, 2311. (f) Basavaiah, D.; Kumaragurabaran, N. Tetrahedron Lett. 2001, 42, 477.
[8] Shi, M. ; Liu, Y. H. Org. Biomol. Chem. 2006, 4, 1468.
[9] Brand, M; Drewes, S. E.; Loizou, G.; Roos, G. H. P. Synth. Commun. 1987, 17, 795.
[10] Shi, M.; Li, C. Q.; Jiang, J. K. Chem. Commun. 2001, 833.
[11] Iwama, T.; Kinoshita, H; Kataoka, T. Tetrahedron Lett. 1999, 40, 3741.
[12] Shi, M.; Jiang, J. K.; Li, C. Q. Tetrahedron Lett. 2001, 43, 127.
[13] Kataoka, T.; Iwama, T; Tsujiyama, S. Chem. Commun. 1998, 197.
[14] Basavaiah, D.; Krishnamacharyulu, M.; Rao, J. Synth. Commun. 2000, 30, 2061.
[15] Yu, C. Z.; Liu, B.; Hu, L. Q. J. Org. Chem. 2001, 66, 5413.
[16] Ameer, F.; Drewes, S. E.; Freese, S.; Kaye, P. T. Synth. Commun. 1988, 18, 495.
[17] Rosa, J. N.; Afonso, C. A. M.; Santos, A. G Tetrahedron 2001, 57, 4189.
[18] Mi, X. L.; Luo, S. Z.; Xu, H; Zhang, L.; Cheng, J. P. Tetrahedron 2006, 62, 2537.
[19] Balan, D.; Adolfsson, H. J. Org. Chem. 2001, 66, 6498.
[20] Kaye, P. T.; Nocanda, X. W. J. Chem. Soc., Perkin Trans. 1 2000, 1331.