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Intercepting the Gold-Catalysed Meyer-Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols

Pennell, MN; Kyle, MP; Gibson, SM; Male, L; Turner, PG; Grainger, RS; Sheppard, TD; (2016) Intercepting the Gold-Catalysed Meyer-Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols. Advanced Synthesis and Catalysis , 358 (9) pp. 1519-1525. 10.1002/adsc.201600101. Green open access

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Abstract

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.

Type: Article
Title: Intercepting the Gold-Catalysed Meyer-Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/adsc.201600101
Publisher version: http://dx.doi.org/10.1002/adsc.201600101
Language: English
Additional information: 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.
Keywords: aldol reaction; alkynes; boronic acids; enolates; gold
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1493120
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