Mild and selective boronic acid catalyzed 1,3-transposition of allylic alcohols and Meyer-Schuster rearrangement of propargylic alcohols

被引：97

作者：

Zheng, Hongchao ^{[1
]}

Lejkowski, Michal ^{[1
]}

Hall, Dennis G. ^{[1
]}

机构：

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

来源：

CHEMICAL SCIENCE | 2011年 / 2卷 / 07期

基金：

加拿大自然科学与工程研究理事会;

关键词：

CARBOXYLIC-ACIDS; ISOMERIZATION; EFFICIENT; 1,3-ISOMERIZATION; CYCLOADDITIONS; TRANSPOSITION; AMIDE; OLEFINATION; STRATEGY;

D O I：

10.1039/c1sc00140j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Boronic acid catalysis (BAC) was applied to the 1,3-transposition of allylic alcohols and the related Meyer-Schuster rearrangement of propargylic alcohols using highly electron deficient polyfluoroarylboronic acids as catalysts under mild metal-free conditions. A wide range of synthetically useful products are formed in E : Z selectivities superior to that of metal-catalyzed methods. A mechanism is proposed involving partial or full ionization into an allylic (or propargylic) carbocation, and additional possibilities for multicatalytic tandem reactions are exemplified.

引用

页码：1305 / 1310

页数：6

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