C3位全碳或胺基取代季碳氧化吲哚的合成新方法研究
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摘要
围绕C3位全碳或胺基取代季碳氧化吲哚的高效构建,本论文发展了从3,3-双双炔丙基取代氧化吲哚出发来不对称催化构建全碳季碳氧化吲哚的新策略；优化了3-潜手性氧化吲哚的不对称胺化反应,成功实现了未保护的3-芳基、3-烷基以及3-杂原子取代氧化吲哚与偶氮二甲酸二叔丁酯(DBAD)的不对称胺化反应,胺化产物可以方便地转化；还发展了酸催化的3-羟基氧化吲哚的傅克反应和Ritter反应,来多样性合成全碳季碳氧化吲哚。具体如下：
1)利用去对称化策略,从3,3-双炔丙基取代氧化吲哚出发,首次实现了高对映选择性的不对称催化CuAAc反应,同时也是首例基于1,6-双炔体系的分子间去对称化反应。在2,5-己二酮作为溶剂,Pybox配体形成的手性Cu(Ⅰ)络合物的催化下,能够以高达82%的收率和98%的对映选择性得到一系列C3位含炔丙基和三氮唑基团的全碳季碳氧化吲哚。产物中的炔基可以方便地进行各种转化。经过核磁共振和非线性效应研究,提出了一种可能的双核铜催化的反应过渡态模型。
2)首次实现了未保护的3烷基或芳基取代的氧化吲哚与DBAD的不对称胺化反应。在1,2-二氯乙烷作为溶剂和5A分子筛的存在下,手性叔胺硫脲双功能催化剂可以催化反应取得高达98%的对映选择性。所得胺化产物可以方便地进行进一步转化。
首次实现了3-杂原子取代的氧化吲哚的不对称胺化反应,合成了一系列C3位N,S或N,O双杂季碳氧化吲哚。在p-ICD或(DHQD)2PYR作为催化剂的情况下,3-硫代或3-氧代氧化吲哚可顺利与DBAD发生不对称胺化反应,取得中等到优秀的收率和对映选择性。产物可转化为结构新颖的双杂原子取代的螺环氧化吲哚。
3)发现使用5mo1%的Hg(ClO4)2-3H2O可以高效地催化系列3-脂肪族或芳香族取代的3-羟基氧化吲哚与苯酚、1,3-二甲氧基苯等苯系芳烃或吲哚、呋喃、噻吩、吡咯等杂芳烃的傅克反应,得到一系列具有非对称结构的3,3-双芳基或3-芳基-3-烷基取代的季碳氧化吲哚。机理研究表明,芳汞化作用产生的芳基汞络合物,不仅可以作为质子酸活化羟基氧化吲哚,同时可以增强富电子芳烃的亲核性,这种新型的双重活化模式是Hg(ClO4)2-3H2O高催化活性的可能原因。
另外,实现了首例3-羟基氧化吲哚与腈类化合物的Ritter反应。廉价易得的HC104可以顺利催化反应进行,以25-95%的收率得到一系列3-酰胺基取代的季碳氧化吲哚。
This thesis focuses on the efficient construction of quaternary oxindoles featuring a C3all-carbon or èV-containing carbon center, which includes the development of a new strategy for the enantioselective synthesis of all-carbon quaternary oxindoles via the catalytic desymmetrization of oxindole based1,6-heptadiynes; the improvement in the catalytic asymmetric direct amination reaction of3-substituted oxindoles, allowing unprotected3-aryl,3-alkyl and3-heteroatom substituted oxindoles to readily react with di-terf-butyl azodicarboxylate (DBAD), which greatly facilitates product elaboration; the diverse synthesis of quaternary oxindoles via acid catalyzed Friedel-Crafts and Ritter reaction of3-substituted3-hydroxyoxindoles. It is divided into the following three parts.
1) The first highly enantioselective Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAc) reaction via asymmetric desymmetrization of oxindole based1,6-heptadiynes is developed, which is also the first highly enantioselective catalytic asymmetric intermolecular desymmetrization of prochiral1,6-dialkynes. Using2,5-hexadione as solvent, a chiral Cu(I) complex derived from Pybox and CuCl allowed the synthesis of quaternary oxindoles bearing both an alkyne and a1,2,3-triazole moiety at the C3position with up to82%yield and98%ee. The thus obtained quaternary oxindoles can be readily elaborated via transformations based on the alkyne group. Based on the NMR studies and negative non-linear effect, a stereochemical model is proposed containing a dinuclear copper intermediate as the catalytically active species.
2) The first example of highly enantioselective direct amination of both unprotected3-aryl and3-alkyloxindoles with DBAD is developed. It is found that the reaction can be efficiently catalyzed by chiral bifunctional tertiary amine-thiourea catalyst with up to98%ee achieved using1,2-dichloroethane (DCE) as solvent and5A MS as additive. The amination adducts can be easily further elaborated.
The highly enantioselective direct amination of3-heteractom substituted oxindoles is also developed for the first time furnishing the3,3-disubstituted oxindoles featuring both sulfur (or oxygen) and nitrogen atoms at C3position. The3-thiooxindoles or3-alkoxyoxindoles can react with DBAD efficiently with moderate to excellent yields and ee values in the presence of β-ICD or (DHQD)2PYR as the catalyst, respectively. The thus obtained amination adducts can be readily transformed to a novel spirocyclic oxindole without the loss of enantioselectivity.
3) The highly efficient Friedel-Crafts reaction of3-aliphatic or aromatic-substituted3-hydroxyoxindoles with a variety of (hetero)aromatic compound, such as phenol,1,3-dimethoxybenzen, indole, furan, thiophene and pyrrole, is developed using only5mol%of Hg(ClO4)2·3H2O as catalyst to synthesis a series of unsymmetrical3,3-diaryloxindoles and3-alkyl-3-aryloxindoles. Mechanism research reveals that the high catalytic property of Hg(ClO4)2·3H2O is originated from the unprecedented dual activation effects of aromatic mercuration, which can generate a strong protic acid to facilitate the generation of carbocation at the C3position of oxindoles and simultaneously form the more reactive nucleophilic reaction partner.
The first Ritter reaction of3-substituted3-hydroxyoxindoles with nitriles, catalyzed by inexpensive and convenient HClO4, is also developed, which enables the synthesis of3-substituted3-aminooxindoles in25-95%yield with rich diversity.
1)利用去对称化策略,从3,3-双炔丙基取代氧化吲哚出发,首次实现了高对映选择性的不对称催化CuAAc反应,同时也是首例基于1,6-双炔体系的分子间去对称化反应。在2,5-己二酮作为溶剂,Pybox配体形成的手性Cu(Ⅰ)络合物的催化下,能够以高达82%的收率和98%的对映选择性得到一系列C3位含炔丙基和三氮唑基团的全碳季碳氧化吲哚。产物中的炔基可以方便地进行各种转化。经过核磁共振和非线性效应研究,提出了一种可能的双核铜催化的反应过渡态模型。
2)首次实现了未保护的3烷基或芳基取代的氧化吲哚与DBAD的不对称胺化反应。在1,2-二氯乙烷作为溶剂和5A分子筛的存在下,手性叔胺硫脲双功能催化剂可以催化反应取得高达98%的对映选择性。所得胺化产物可以方便地进行进一步转化。
首次实现了3-杂原子取代的氧化吲哚的不对称胺化反应,合成了一系列C3位N,S或N,O双杂季碳氧化吲哚。在p-ICD或(DHQD)2PYR作为催化剂的情况下,3-硫代或3-氧代氧化吲哚可顺利与DBAD发生不对称胺化反应,取得中等到优秀的收率和对映选择性。产物可转化为结构新颖的双杂原子取代的螺环氧化吲哚。
3)发现使用5mo1%的Hg(ClO4)2-3H2O可以高效地催化系列3-脂肪族或芳香族取代的3-羟基氧化吲哚与苯酚、1,3-二甲氧基苯等苯系芳烃或吲哚、呋喃、噻吩、吡咯等杂芳烃的傅克反应,得到一系列具有非对称结构的3,3-双芳基或3-芳基-3-烷基取代的季碳氧化吲哚。机理研究表明,芳汞化作用产生的芳基汞络合物,不仅可以作为质子酸活化羟基氧化吲哚,同时可以增强富电子芳烃的亲核性,这种新型的双重活化模式是Hg(ClO4)2-3H2O高催化活性的可能原因。
另外,实现了首例3-羟基氧化吲哚与腈类化合物的Ritter反应。廉价易得的HC104可以顺利催化反应进行,以25-95%的收率得到一系列3-酰胺基取代的季碳氧化吲哚。
This thesis focuses on the efficient construction of quaternary oxindoles featuring a C3all-carbon or èV-containing carbon center, which includes the development of a new strategy for the enantioselective synthesis of all-carbon quaternary oxindoles via the catalytic desymmetrization of oxindole based1,6-heptadiynes; the improvement in the catalytic asymmetric direct amination reaction of3-substituted oxindoles, allowing unprotected3-aryl,3-alkyl and3-heteroatom substituted oxindoles to readily react with di-terf-butyl azodicarboxylate (DBAD), which greatly facilitates product elaboration; the diverse synthesis of quaternary oxindoles via acid catalyzed Friedel-Crafts and Ritter reaction of3-substituted3-hydroxyoxindoles. It is divided into the following three parts.
1) The first highly enantioselective Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAc) reaction via asymmetric desymmetrization of oxindole based1,6-heptadiynes is developed, which is also the first highly enantioselective catalytic asymmetric intermolecular desymmetrization of prochiral1,6-dialkynes. Using2,5-hexadione as solvent, a chiral Cu(I) complex derived from Pybox and CuCl allowed the synthesis of quaternary oxindoles bearing both an alkyne and a1,2,3-triazole moiety at the C3position with up to82%yield and98%ee. The thus obtained quaternary oxindoles can be readily elaborated via transformations based on the alkyne group. Based on the NMR studies and negative non-linear effect, a stereochemical model is proposed containing a dinuclear copper intermediate as the catalytically active species.
2) The first example of highly enantioselective direct amination of both unprotected3-aryl and3-alkyloxindoles with DBAD is developed. It is found that the reaction can be efficiently catalyzed by chiral bifunctional tertiary amine-thiourea catalyst with up to98%ee achieved using1,2-dichloroethane (DCE) as solvent and5A MS as additive. The amination adducts can be easily further elaborated.
The highly enantioselective direct amination of3-heteractom substituted oxindoles is also developed for the first time furnishing the3,3-disubstituted oxindoles featuring both sulfur (or oxygen) and nitrogen atoms at C3position. The3-thiooxindoles or3-alkoxyoxindoles can react with DBAD efficiently with moderate to excellent yields and ee values in the presence of β-ICD or (DHQD)2PYR as the catalyst, respectively. The thus obtained amination adducts can be readily transformed to a novel spirocyclic oxindole without the loss of enantioselectivity.
3) The highly efficient Friedel-Crafts reaction of3-aliphatic or aromatic-substituted3-hydroxyoxindoles with a variety of (hetero)aromatic compound, such as phenol,1,3-dimethoxybenzen, indole, furan, thiophene and pyrrole, is developed using only5mol%of Hg(ClO4)2·3H2O as catalyst to synthesis a series of unsymmetrical3,3-diaryloxindoles and3-alkyl-3-aryloxindoles. Mechanism research reveals that the high catalytic property of Hg(ClO4)2·3H2O is originated from the unprecedented dual activation effects of aromatic mercuration, which can generate a strong protic acid to facilitate the generation of carbocation at the C3position of oxindoles and simultaneously form the more reactive nucleophilic reaction partner.
The first Ritter reaction of3-substituted3-hydroxyoxindoles with nitriles, catalyzed by inexpensive and convenient HClO4, is also developed, which enables the synthesis of3-substituted3-aminooxindoles in25-95%yield with rich diversity.
引文
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