Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine

被引：240

作者：

Andrey, O ^{[1
]}

Alexakis, A ^{[1
]}

Bernardinelli, G ^{[1
]}

机构：

[1] Univ Geneva, CH-1211 Geneva, Switzerland

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 14期

关键词：

D O I：

10.1021/ol0348755

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] The regio-, stereo-, and enantioselective direct Michael addition of alpha-hydroxyketones to beta-aryinitroolef ins catalyzed by N-/Pr-2,2'-bipyrrolidine is described. The formation of an internal hydrogen bond between the OH group of alpha-hydoxyacetone and the tertiary nitrogen of the catalyst leads to the formation of a rigid cis enamine intermediate that explains the inversion of the expected diastereoselectivity and the very high ee's.

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页码：2559 / 2561

页数：3

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