L-Prolinethioamides - Efficient organocatalysts for the direct asymmetric aldol reaction

被引:85
|
作者
Gryko, D [1 ]
Lipinski, R [1 ]
机构
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
关键词
asymmetric aldol reaction; C-C bond formation; organic catalysis; proline; thioamides;
D O I
10.1002/adsc.200505247
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A series of novel L-proline derived thioamides has been synthesised. They have been evaluated as organocatalysts in the direct asymmetric aldol reaction for the first time. Thioamides exhibit catalytic ability higher than proline itself and the model aldol reaction of 4-cyanobenzaldehyde with acetone proceeds well in the presence of 5 mol % of catalyst (ee up to 100%). Other aromatic aldehydes gave aldol products with high ees and moderate yields. Small changes in the catalyst's structure [e.g., N-Bn versus N-CH(CH3)Ph] as well as the addition of an acid have a profound effect on their activity. The unexpected formation of the catalyst-derived cyclic adducts was observed and their reactivity was established giving valuable insight into the course of the reaction.
引用
收藏
页码:1948 / 1952
页数:5
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