%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.