Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether

被引：135

作者：

Zu, Liansuo

Li, Hao

Wang, Jian

Yu, Xinhong ^{[1
]}

Wang, Wei

机构：

[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA

[2] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 29期

关键词：

asymmetric organocatalysis; diphenylpyrrolinol silyl ether; fluorous chemistry; Michael addition reaction; nitroolefin;

D O I：

10.1016/j.tetlet.2006.05.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A recyclable and reusable (S) diphenylpyrrolinol silyl ether I organocatalyst bearing a n-C8F17 fluorous tag has been demonstrated for promoting the asymmetric Michael addition reactions of a wide range of aldehydes with both aryl and alkyl-substituted nitroolefins and excellent levels of enantio- and diastereoselectivities are achieved. The catalyst I can be conveniently recovered by fluorous solid-phase extraction and subsequently reused (up to eight cycles) without significant loss of its catalytic activity and stereoselectivity for the process. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5131 / 5134

页数：4

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