Density functional theory study of the 5-pyrrolidin-2-yltetrazole-catalyzed aldol reaction

被引：37

作者：

Arnó, M ^{[1
]}

Zaragozá, RJ ^{[1
]}

Domingo, LR ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, Inst Ciencia Mol UIQOT, E-46100 Burjassot, Valencia, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 16期

关键词：

D O I：

10.1016/j.tetasy.2005.06.034

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The replacement of the carboxylic acid functionality with a tetrazolic acid in the proline-catalyzed asymmetric aldol reaction between acetone and trimethylacetaldehyde has been studied using DFT methods at the B3LYP/6-31G** computational level. For the C-C bond-formation step, four reactive channels corresponding to the syn and anti arrangement of the enamine and the re and si attack modes have been analyzed. The B3LYP/6-31G** results allowed us to explain the stereo selectivity and the increase in reactivity relative to the proline-catalyzed process in DMSO. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2764 / 2770

页数：7

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