The origin of stereoselectivity in primary amino acid catalyzed intermolecular Aldol reactions

被引：125
作者：
Bassan, A
Zou, WB
Reyes, E
Himo, F [1 ]
Córdova, A
机构：
[1] Royal Inst Technol, Dept Theoret Chem, ALBANOVA, S-10691 Stockholm, Sweden
[2] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
[3] Univ Stockholm, Dept Phys, S-10691 Stockholm, Sweden
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 43期
关键词：
aldol reaction; amino acids; asymmetric catalysis; density functional calculations; transition states;
D O I：
10.1002/anie.200502388
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Combined forces: Theory and experiment are used together to determine the mechanism of primary amino acid catalyzed intermolecular aldol reactions. A six-membered chairlike structure is determined to be the transition state for the reaction between benzaldehyde and cyclohexanone catalyzed by (S)-alanine (see scheme), and a carboxylic acid catalyzed enamine mechanism is shown to be the most favorable reaction pathway. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
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收藏
页码：7028 / 7032
页数：5
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