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

Research output: Contribution to journalArticle

Authors

  • Matthew Pennell
  • Michael Kyle
  • Samantha Gibson
  • Louise Male
  • Peter Turner
  • Tom Sheppard

Colleges, School and Institutes

External organisations

  • University College London
  • GlaxoSmithKline

Abstract

The regioselective gold-catalysed hydration of propargylic alcohols to beta-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 para-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.

Details

Original languageEnglish
Pages (from-to)1519-1525
Number of pages7
JournalAdvanced Synthesis & Catalysis
Volume358
Issue number9
Early online date27 Apr 2016
Publication statusPublished - 28 Apr 2016

Keywords

  • aldol reaction, alkynes, boronic acids, enolates, gold