Gold-mediated synthesis of alpha-ionone

Valentina Merlini, Sylvain Gaillard, Alessio Porta, Giuseppe Zanoni, Giovanni Vidari, Steven P. Nolan

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

A simple and convenient synthesis of a-ionone, an important component of flowers and fragrances, is reported. The key step in the formation of the a.,p-unsaturated ketone moiety involves an NHC-Au-1 catalyzed Meyer-Schuster-like rearrangement of readily prepared propargylic esters. The complex [{Au(IPr)}(2)(mu-OH)][BF4] proved to be the most efficient catalyst leading to a-ionone in 70% yield from a propargylic benzoate. This optimized procedure represents a valuable and attractive alternative to classical methods leading to alpha,beta-unsaturated ketones, such as the Wittig or aldol reactions. (C) 2011 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1124-1127
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number10
DOIs
Publication statusPublished - 9 Mar 2011

Keywords

  • Ionone
  • Gold catalysis
  • Meyer-Schuster rearrangement
  • Propargylic esters
  • NHC
  • MEYER-SCHUSTER REARRANGEMENT
  • ENANTIOSELECTIVE SYNTHESIS
  • CATALYSIS
  • EFFICIENT
  • DERIVATIVES
  • CARBINOLS
  • COMPLEXES
  • MECHANISM
  • FORSKOLIN
  • VERSATILE

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