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
收藏
页码：2378 / 2382
页数：5
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