Recent Advances in Chiral Phosphoric Acid Catalyzed Asymmetric Reactions for the Synthesis of Enantiopure Indole Derivatives

被引:154
|
作者
Wu, Hua [1 ]
He, Yu-Ping [1 ]
Shi, Feng [2 ,3 ]
机构
[1] Shandong Univ Technol, Sch Chem Engn, Zibo 255049, Peoples R China
[2] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China
[3] Jiangsu Normal Univ, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Peoples R China
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 14期
关键词
chiral indole derivatives; chiral phosphoric acids; asymmetric reactions; addition reactions; cycloaddition reactions; cascade reactions; FRIEDEL-CRAFTS ALKYLATION; DIELS-ALDER REACTIONS; N-TRIFLYL PHOSPHORAMIDE; ORTHO-QUINONE METHIDES; BRONSTED-ACID; ENANTIOSELECTIVE SYNTHESIS; TRANSFER HYDROGENATION; RELAY CATALYSIS; METAL CATALYSIS; ORGANOCATALYTIC CONSTRUCTION;
D O I
10.1055/s-0034-1378837
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral indole derivatives are an intriguing class of heterocyclic compounds; their structural motifs are frequently found in natural products and synthetic compounds with significant bioactivity. Among many synthetic transformations leading to the production of enantiopure indole derivatives, chiral phosphoric acid catalyzed reactions are the most attractive methodologies, since these reactions can directly afford enantiomerically pure indole derivatives from readily accessible starting materials under mild conditions. In this review, the most recent achievements in this research area have been gathered and classified according to different reaction types for the synthesis of enantioenriched indole derivatives under the catalysis of chiral phosphoric acids. 1 Introduction 2 Chiral Phosphoric Acid Catalyzed Asymmetric Addition Reactions 2.1 1,2-Addition Reactions 2.2 1,4-Addition Reactions 3 Chiral Phosphoric Acid Catalyzed Asymmetric Cycloaddition Reactions 3.1 [3+2] Reactions 3.2 [4+2] Reactions 3.3 [3+3] Reactions 4 Chiral Phosphoric Acid Catalyzed Asymmetric Cascade Reactions 4.1 Cascade Reactions 4.2 Transition-Metal-Cocatalyzed Cascade Reactions 4.3 Other Organocatalyst-Cocatalyzed Cascade Reactions 5 Other Reactions Catalyzed by Chiral Phosphoric Acids 5.1 Aza-Claisen Rearrangement 5.2 Kinetic Resolution 5.3 Fischer Indolization 6 Conclusions and Perspective
引用
收藏
页码:1990 / 2016
页数:27
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