Highly Active Water-Soluble and Recyclable Organocatalyst for the Asymmetric 1,4-Conjugate Addition of Nitroalkanes to α,β-Unsaturated Aldehydes

被引：48

作者：

Ghosh, Subrata K. ^{[1
]}

Zheng, Zilong ^{[1
]}

Ni, Bukuo ^{[1
]}

机构：

[1] Texas A&M Univ Commerce, Dept Chem, Commerce, TX 75429 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 14-15期

关键词：

aldehydes; asymmetric catalysis; catalyst recycling; C-C bond formation; Michael addition; ENANTIOSELECTIVE MICHAEL ADDITION; SILYL ETHER; CONJUGATE ADDITION; ORGANIC-CHEMISTRY; EFFICIENT; NITROOLEFINS; CATALYSTS; KETONES; ACTIVATION; BACLOFEN;

D O I：

10.1002/adsc.201000344

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel strategy for the catalytic asymmetric conjugate addition of nitroalkanes to alpha,beta-unsaturated aldehydes in aqueous media has been developed by using diarylprolinol silyl ether in combination with benzoic acid as a water-soluble organocatalyst providing the desired adducts in good to excellent enantioselectivities (up to 95% ee). This catalyst can be recycled at least five times with only a slight reduction in activity and selectivity. In addition, the synthetic procedure presented is simple, practical and environmentally benign.

引用

页码：2378 / 2382

页数：5

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