Biomimetic asymmetric aldol reactions catalyzed by proline derivatives attached to β-cyclodextrin in water

被引：32

作者：

Shen, Hai-Min ^{[1
]}

Ji, Hong-Bing ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 28期

基金：

中国国家自然科学基金;

关键词：

beta-Cyclodextrin; Proline derivative; Asymmetric aldol reaction; Quantum calculation; EFFICIENT; KETONES; ORGANOCATALYST;

D O I：

10.1016/j.tetlet.2012.04.140

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two proline derivatives, (S)-2-aminomethylpyrrolidine and (R)-2-aminomethylpyrrolidine modified beta-CD (CD-1, CD-2) were synthesized in the yields of 31% and 14%. Their self-inclusion conformations were characterized by H-1 ROESY NMR studies and quantum calculation. When CD-1 was applied to asymmetric aldol reactions, up to 94% ee was obtained. Substrate selectivity was also observed in these asymmetric aldol reactions. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3541 / 3545

页数：5

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