Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: Unprecedented regiocontrol in aqueous media

被引:227
作者
Tang, Z [1 ]
Yang, ZH
Cun, LF
Gong, LZ
Mi, AQ
Jiang, YZ
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Union Lab Asymmetr Synth, Chengdu 610041, Peoples R China
[3] Chinese Acad Sci, Grad Sch, Beijing, Peoples R China
关键词
D O I
10.1021/ol049141m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] L-Proline-based small peptides have been developed as efficient catalysts for the asymmetric direct aldol reactions of hydroxyacetone with aldehydes. Chiral 1,4-diols 7, which are disfavored products in similar aldol reactions catalyzed by either aldolases or L-proline, were obtained in high yields and enantioselectivities of up to 96% ee with peptides 3 and 4 in aqueous media.
引用
收藏
页码:2285 / 2287
页数:3
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