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.

引用

页码：7028 / 7032

页数：5

共 46 条

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