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
收藏
页码：3541 / 3545
页数：5
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