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Issue 7, 2011
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Mild and selective boronic acid catalyzed 1,3-transposition of allylic alcohols and Meyer–Schuster rearrangement of propargylic alcohols

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Abstract

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.

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

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Article information


Submitted
10 Mar 2011
Accepted
05 Apr 2011
First published
21 Apr 2011

Chem. Sci., 2011,2, 1305-1310
Article type
Edge Article

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

H. Zheng, M. Lejkowski and D. G. Hall, Chem. Sci., 2011, 2, 1305
DOI: 10.1039/C1SC00140J

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