N-Heterocyclic Carbene and Bronsted Acid Cooperative Catalysis: Asymmetric Synthesis of trans-γ-Lactams

被引：247

作者：

Zhao, Xiaodan ^{[1
]}

DiRocco, Daniel A. ^{[1
]}

Rovis, Tomislav ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 32期

关键词：

INTERMOLECULAR STETTER REACTION; STEREOSELECTIVE-SYNTHESIS; DIRECT ANNULATIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; NUCLEOPHILIC CARBENE; EFFICIENT SYNTHESIS; CONJUGATE UMPOLUNG; ENALS; IMINES; METAL;

D O I：

10.1021/ja205714g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient enantioselective approach to form trans-gamma-lactams in up to 99% yield, 93% ee, and >20/1 dr using unactivated imines has been developed. The cyclohexyl-substituted azolium and the weak base sodium o-chlorobenzoate are most suitable for this transformation. Notably, the process involves cooperative catalysis by an N-heterocyclic carbene and a Bronsted acid.

引用

页码：12466 / 12469

页数：4

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