Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency

被引：74

作者：

Chen, Jia-Rong ^{[1
]}

Cao, Yi-Ju ^{[1
]}

Zou, You-Quan ^{[1
]}

Tan, Fen ^{[1
]}

Fu, Liang ^{[1
]}

Zhu, Xiao-Yu ^{[1
]}

Xiao, Wen-Jing ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 06期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE MICHAEL ADDITION; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; BETA-UNSATURATED ALDEHYDES; ORGANIC CATALYSIS; 1,3-DICARBONYL COMPOUNDS; PYRROLIDINE-THIOUREA; UNMODIFIED ALDEHYDES; CARBONYL-COMPOUNDS; NITRO-MICHAEL; KETONES;

D O I：

10.1039/b925962g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of thiourea-amine bifunctional catalysts have been developed by a rational combination of prolines with cinchona alkaloids, which are connected by a thiourea motif. The catalyst 3a, prepared from L-proline and cinchonidine, was found to be a highly efficient catalyst for the conjugate addition of ketones/aldehydes to a wide range of nitroalkenes (up to 98/2 dr and 96% ee). The privileged cinchonidine backbone and the thiourea motif are essential to the reaction activity and enantioselectivity.

引用

页码：1275 / 1279

页数：5

共 118 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].