Asymmetric conjugate addition of carbonyl compounds to nitroalkenes catalyzed by chiral bifunctional thioureas

被引：66

作者：

Zhang, Xue-jing ^{[1
]}

Liu, Sheng-ping ^{[1
]}

Lao, Jin-hua ^{[1
]}

Du, Guang-jian ^{[1
]}

Yan, Ming ^{[1
]}

Chan, Albert S. C. ^{[1
,2
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Ind Inst Fine Chem & Synth Drugs, Guangzhou 510006, Guangdong, Peoples R China

[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 12期

基金：

中国国家自然科学基金;

关键词：

ORGANOCATALYTIC MICHAEL ADDITION; ALDOL REACTIONS; GAMMA(2)-AMINO ACIDS; ENAMINE CATALYSIS; RATIONAL APPROACH; AMINE CATALYSTS; SYN-ALDOL; ALDEHYDES; KETONES; WATER;

D O I：

10.1016/j.tetasy.2009.06.003

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Readily available chiral thioureas derived from cyclohexane-1,2-diamine were prepared and found to be highly effective organocatalysts for the Conjugate addition of aldehydes and ketones to nitroalkenes. Excellent enantioselectivities and yields were obtained for a variety of aryl and heteroaryl nitroalkenes. The base additives are essential for good yields and excellent enantioselectivities in this transformation. Based oil new experimental evidence, a modified catalytic mechanism was proposed to rationalize the important role of the base additives. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1451 / 1458

页数：8

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