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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 19期

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

页码：3155 / 3160

页数：6

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