%0 Journal Article
%@ 1615-4169
%A Pennell, MN
%A Kyle, MP
%A Gibson, SM
%A Male, L
%A Turner, PG
%A Grainger, RS
%A Sheppard, TD
%D 2016
%F discovery:1493120
%J Advanced Synthesis and Catalysis
%K aldol reaction; alkynes; boronic acids; enolates; gold
%N 9
%P 1519-1525
%T Intercepting the Gold-Catalysed Meyer-Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols
%U https://discovery.ucl.ac.uk/id/eprint/1493120/
%V 358
%X The regioselective gold-catalysed hydration of propargylic alcohols to β-hydroxy ketones can be achieved by diverting the gold-catalysed Meyer-Schuster rearrangement through the addition of a protic additive with a pKa of 7-9 such as p-nitrophenol, boric acid or a boronic acid. This provides an interesting alternative to an aldol reaction when combined with the straightforward addition of an alkyne to an aldehyde or ketone. The gold-catalysed reaction of an electron-deficient, sterically hindered propargylic alcohol with a boronic acid led to the formation of an unusually stable cyclic boron enolate.
%Z Copyright © 2016 The author. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Licence (http://creativecommons.org/licenses/by/4.0/), which permits use, distribution and reproduction in any medium provided the original work is properly cited.