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.
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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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