Highly enantioselective conjugate addition of 1-bromonitroalkanes to α,β-unsaturated ketones catalyzed by 9-amino-9-deoxyepiquinine

被引：32

作者：

Dong, Li-ting ^{[1
]}

Lu, Rui-jiong ^{[1
]}

Du, Quan-sheng ^{[1
]}

Zhang, Jun-min ^{[1
]}

Liu, Sheng-ping ^{[1
]}

Xuan, Yi-ning ^{[1
]}

Yan, Ming ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2009年 / 65卷 / 21期

基金：

中国国家自然科学基金;

关键词：

9-Amino-9-deoxyepiquinine; Organocatalysis; Conjugate addition; 1-Bromonitroalkane; alpha; beta-Unsaturated ketone; ASYMMETRIC MICHAEL ADDITION; MULTISUBSTITUTED CYCLOPENTANES; NITROCYCLOPROPANATION REACTION; HENRY REACTION; PRIMARY AMINES; CYCLIC ENONES; ORGANOCATALYSIS; NITROALKANES; ALPHA; STEREOCENTERS;

D O I：

10.1016/j.tet.2009.03.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric conjugate addition of 1-bromonitroalkanes to alpha,beta-unsaturated ketones was studied using chiral primary amines as the catalysts. 9-Amino-9-deoxyepiquinine was found to be highly efficient catalyst for the transformation. 4-Bromo-4-nitroketones were obtained with excellent enantioselectivities (97-99% ee) and good yields (61-99%) for a variety of alkyl vinyl ketones. The product could be further debrominated with Bu3SnH/AlBN to provide chiral 4-nitroketones in good yield and without loss of the optical purity. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：4124 / 4129

页数：6

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