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  -