TY - JOUR IS - 9 EP - 1525 A1 - Pennell, MN A1 - Kyle, MP A1 - Gibson, SM A1 - Male, L A1 - Turner, PG A1 - Grainger, RS A1 - Sheppard, TD KW - aldol reaction; alkynes; boronic acids; enolates; gold VL - 358 TI - Intercepting the Gold-Catalysed Meyer-Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols Y1 - 2016/04/28/ AV - public SP - 1519 SN - 1615-4169 N2 - The regioselective gold-catalysed hydration of propargylic alcohols to ?-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. JF - Advanced Synthesis and Catalysis N1 - 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. ID - discovery1493120 UR - http://dx.doi.org/10.1002/adsc.201600101 ER -