A New Organocatalyzed Michael-Michael Cascade Reaction Generates Highly Substituted Fused Carbocycles

被引：39

作者：

McGarraugh, Patrick G.

Brenner, Stacey E. ^{[1
]}

机构：

[1] CUNY Brooklyn Coll, Dept Chem, Brooklyn, NY 11210 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 24期

基金：

美国国家卫生研究院;

关键词：

DIPHENYLPROLINOL SILYL ETHER; ALPHA; BETA-UNSATURATED ALDEHYDES; ASYMMETRIC-SYNTHESIS; ALDOL CONDENSATION; DOMINO; CYCLOPENTANES; STEREOCENTERS;

D O I：

10.1021/ol9024293

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

While beta-ketoesters are useful Michael donors, they were previously ineffective in Michael-Michael cascade reactions using alpha,beta-unsaturated aldehydes in conjunction with diphenylprolinol silyl ether organocatalysts. However, through rational modification of substrates and manipulation of the catalytic cycle, we developed an efficient Michael-Michael cascade reaction using beta-ketoesters of type 9. In this transformation, highly substituted fused carbocycles are generated in a single step in up to 87% yield and 99% ee.

引用

页码：5654 / 5657

页数：4

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