The Catalytic Asymmetric Intramolecular Stetter Reaction

被引:179
作者
de Alaniz, Javier Read [1 ]
Rovis, Tomislav [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
基金
美国国家卫生研究院;
关键词
asymmetric synthesis; triazolium salts; quaternary stereocenters; carbene catalysis; nucleophilic catalysis; organocatalysis; Stetter reaction; benzoin reaction; N-HETEROCYCLIC CARBENES; BICYCLIC THIAZOLIUM SALTS; ACYL ANION EQUIVALENTS; BENZOIN CONDENSATION; ENANTIOSELECTIVE SYNTHESIS; QUATERNARY STEREOCENTERS; CONJUGATE ADDITION; NUCLEOPHILIC CARBENES; 2+2+2 CYCLOADDITION; EFFICIENT SYNTHESIS;
D O I
10.1055/s-0029-1216654
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This Account chronicles our efforts in the development of the catalytic asymmetric Stetter reaction using chiral triazolium salts as small molecule organic catalysts. Advances in the mechanistically related azolium-catalyzed asymmetric benzoin reaction are discussed, particularly as they apply to catalyst design. A chronological treatise of reaction discovery, catalyst optimization and reactivity extension follows.
引用
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页码:1189 / 1207
页数:19
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