Lewis acids catalyze the addition of allylboronates to aldehydes by electrophilic activation of the dioxaborolane in a closed transition structure

被引：102

作者：

Rauniyar, V ^{[1
]}

Hall, DG ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 14期

关键词：

D O I：

10.1021/ja049446w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This study addressed the mechanism of the recently reported Lewis acid-catalyzed manifold for additions of allylboronates to aldehydes. A series of control experiments using various reagents and conditions, and kinetic studies by low-temperature NMR spectroscopy, were performed to investigate the origin of the activation provided by the best catalyst, Sc(OTf)3. The results obtained are strongly supportive of a mechanism involving electrophilic boron activation by coordination of the metal ion to one of the boronate oxygens in a closed bimolecular transition state. Copyright © 2004 American Chemical Society.

引用

页码：4518 / 4519

页数：2

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