Highly enantioselective reduction of β,β-disubstituted aromatic nitroalkenes catalyzed by Clostridium sporogenes

被引:73
作者
Fryszkowska, Anna [1 ]
Fisher, Karl [1 ]
Gardiner, John M. [1 ]
Stephens, Gill M. [1 ]
机构
[1] Univ Manchester, Manchester Interdisciplinary Bioctr, Manchester M1 7DN, Lancs, England
基金
英国生物技术与生命科学研究理事会;
关键词
D O I
10.1021/jo800124v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This is the first report of the use of Clostridium sporogenes extracts for enantioselective reduction of C = C double bonds of beta,beta-disubstituted (1) and alpha,beta-disubstituted nitroalkenes (3). Crude enzyme preparations reduced aryl derivatives la-e and 1h, in 35-86% yield with >= 97% ee. Reduction of (E)- and (Z)-isomers of 1c gave the same enantiomer of 2c (>= 99% ee). In contrast, alpha,beta-disubstituted nitroalkene 3a was a poor substrate, yielding (S)-4a in low yield (10-20%), and the ee (30-70% ee) depended on NADH concentration. An efficient synthesis of a library of nitroalkenes I is described.
引用
收藏
页码:4295 / 4298
页数:4
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