Gold-mediated synthesis of α-ionone

V Merlini, S Gaillard, A Porta, G Zanoni, G Vidari…

Index: Merlini, Valentina; Gaillard, Sylvain; Porta, Alessio; Zanoni, Giuseppe; Vidari, Giovanni; Nolan, Steven P. Tetrahedron Letters, 2011 , vol. 52, # 10 p. 1124 - 1127

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Citation Number: 21

Abstract

A simple and convenient synthesis of α-ionone, an important component of flowers and fragrances, is reported. The key step in the formation of the α, β-unsaturated ketone moiety involves an NHC-AuI catalyzed Meyer–Schuster-like rearrangement of readily prepared propargylic esters. The complex [{Au (IPr)} 2 (μ-OH)][BF4] proved to be the most efficient catalyst leading to α-ionone in 70% yield from a propargylic benzoate. This optimized ...