L-Prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins

被引：21
|
作者：
Chua, Pei Juan [1 ]
Tan, Bin [1 ]
Zeng, Xiaofei [1 ]
Zhong, Guofu [1 ]
机构：
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 14期
关键词：
Organocatalytic; Asymmetric Michael addition; Prolinol catalysis; Nitroolefin; Cyclohexanone; ASYMMETRIC ALDOL REACTIONS; ORGANOCATALYTIC CONJUGATE ADDITION; STEREOSELECTIVE ORGANOCATALYST; ALPHA; BETA-UNSATURATED KETONES; MULTISUBSTITUTED CYCLOPENTANES; QUATERNARY STEREOCENTERS; PYRROLIDINE SULFONAMIDE; NITRO-OLEFINS; ALDEHYDES; NITROALKENES;
D O I：
10.1016/j.bmcl.2009.03.076
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Though many chiral amines such as L-proline and its derivatives have proven to be versatile catalysts in many reactions, L-prolinol was seldom used as organocatalyst for reactions. Herein, we report the first L-prolinol catalyzed asymmetric Michael addition of cyclohexanone to nitroolefins in the presence of benzoic acid to afford Michael adducts with high diastereoselectivities (87:13->99:1) and enantioselectivities (82-96%). (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3915 / 3918
页数：4
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