Pyrrolidine-Camphor Derivative as an Organocatalyst for Asymmetic Michael Additions of α,α-Disubstituted Aldehydes to β-Nitroalkenes: Construction of Quaternary Carbon-Bearing Aldehydes under Solvent-Free Conditions

被引：63

作者：

Chang, Chihliang ^{[1
]}

Li, Ssu-Hsien ^{[1
]}

Reddy, Raju Jannapu ^{[1
]}

Chen, Kwunmin ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 09期

关键词：

asymmetric catalysis; Michael reaction; beta-nitroalkenes; quaternary carbon centers; solvent-free reaction; CONJUGATE ADDITION; ENANTIOSELECTIVE CONSTRUCTION; ORGANIC-REACTIONS; EFFICIENT; KETONES; NITROOLEFINS; CATALYSTS; WATER; THIOUREA; PROLINE;

D O I：

10.1002/adsc.200800771

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel pyrrolidine-camphor organocatalyst 3 was designed, synthesized and proven to be an efficient catalyst for the asymmetric Michael reaction. Treatment of alpha,alpha-disubstituted aldehydes with beta-nitroalkenes in the presence of 20 mol% organocatalyst 3 and 20 mol% benzoic acid under solvent-free conditions provided the desired Michael product possessing an all-carbon quaternary center with high chemical yields (up to 99% yield) and high levels of enantioselectivities (up to 95% ee).

引用

页码：1273 / 1278

页数：6

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