An ab initio molecular orbital study on the Lewis acidity of TMS-Cl and TMS-CN toward an alpha,beta-unsaturated aldehyde: Are these acid-base interactions important in organocuprate 1,4-additions to enones?

被引：20

作者：

Lipshutz, BH

Aue, DH

James, B

机构：

[1] Department of Chemistry, University of California, Santa Barbara

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 47期

关键词：

D O I：

10.1016/0040-4039(96)01969-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High-level ab initio calculations were used to determine the effectiveness of commonly used silanes as Lewis acids toward acrolein as a model for Gilman cuprate conjugate addition reactions. The data suggest that complexation with an enone is by a weak dipole-dipole interaction and is not directly responsible for the rate accelerating effect of TMS-X. Copyright (C) 1996 Elsevier Science Ltd

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页码：8471 / 8474

页数：4

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