Enantioselective, NHC-Catalyzed bicyclo-β-lactam formation via direct annulations of enals and unsaturated N-sulfonyl ketimines

被引：211

作者：

He, Ming ^{[1
]}

Bode, Jeffrey W. ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 02期

关键词：

D O I：

10.1021/ja0778592

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A wide range of alpha,beta-unsaturated aldehydes induding 3-alkyl derivatives undergo N-heterocyclic carbene (NHC)-catalyzed annulations with N-sulfonyl ketimines under mild condition, to provide bicyclo[3.2.0]lactams with outstanding diastereo- and enantioselectivity. This concise route to beta-lactams established four new chiral centers in a single operation. Although this process could occur via the intermediacy of a catalytically generated homoenolate equivalent, the stereochemical outcome supports a tandem or concerted aza-Benzoin/oxy-Cope reaction as the key bond forming step.

引用

页码：418 / +

页数：3