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

Hongchao Zheng; Michal Lejkowski; Dennis G. Hall

doi:10.1039/C1SC00140J

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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

Hongchao Zheng,^a Michal Lejkowski^a and Dennis G. Hall*^a

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Department of Chemistry, University of Alberta, Edmonton, Canada
E-mail: dennis.hall@ualberta.ca

Chem. Sci., 2011,2, 1305-1310

DOI: 10.1039/C1SC00140J
Received 10 Mar 2011, Accepted 05 Apr 2011
First published online 21 Apr 2011

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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.

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

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