Evaluation of 6-APA as a New Organocatalyst for a Direct Cross-Aldol Reaction

被引:9
|
作者
Emer, Enrico [1 ]
Galletti, Paola [1 ]
Giacomini, Daria [1 ]
机构
[1] Univ Bologna, Dept Chem G Ciamician, I-40126 Bologna, Italy
关键词
Asymmetric catalysis; Aldol reactions; Penicillins; Organocatalysis; ASYMMETRIC ORGANOCATALYSIS; AMINO-ACIDS; WATER; CATALYST; DISCOVERY; PROLINE;
D O I
10.1002/ejoc.200900181
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
6-Aminopenicillanic acid (6-APA) and two of its derivatives, 6-APA benzyl ester (6-APA-OBn) and Penicillin G (PenG), have been evaluated as catalysts for use in direct cross-aldol reactions in different solvents and mixtures. The effects of catalyst loading, reaction time, pH and temperature on the yield and stereoselectivity have been studied, 6-APA proved to be an effective catalyst in terms of yield for the reaction between cyclohexanone and p-nitrobenzaldehyde, especially in neat conditions. The stereoselectivity of the reaction was conditioned by the presence of two competing mechanisms: one an imine-enamine pathway and the other a Bronsted acid catalysis. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码:3155 / 3160
页数:6
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