Gold-mediated synthesis of alpha-ionone

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

doi:10.1016/j.tetlet.2011.01.010

Gold-mediated synthesis of alpha-ionone

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	1124-1127
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2011.01.010
Publication status	Published - 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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10.1016/j.tetlet.2011.01.010

Molecular assembly using gold catalysis: Molecular assembly using gold catalysis
Nolan, S. P. (PI)
EPSRC
1/01/10 → 31/12/12
Project: Standard

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title = "Gold-mediated synthesis of alpha-ionone",

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.",

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

author = "Valentina Merlini and Sylvain Gaillard and Alessio Porta and Giuseppe Zanoni and Giovanni Vidari and Nolan, {Steven P.}",

year = "2011",

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doi = "10.1016/j.tetlet.2011.01.010",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Gold-mediated synthesis of alpha-ionone

AU - Merlini, Valentina

AU - Gaillard, Sylvain

AU - Porta, Alessio

AU - Zanoni, Giuseppe

AU - Vidari, Giovanni

AU - Nolan, Steven P.

PY - 2011/3/9

Y1 - 2011/3/9

N2 - 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.

AB - 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.

KW - Ionone

KW - Gold catalysis

KW - Meyer-Schuster rearrangement

KW - Propargylic esters

KW - NHC

KW - MEYER-SCHUSTER REARRANGEMENT

KW - ENANTIOSELECTIVE SYNTHESIS

KW - CATALYSIS

KW - EFFICIENT

KW - DERIVATIVES

KW - CARBINOLS

KW - COMPLEXES

KW - MECHANISM

KW - FORSKOLIN

KW - VERSATILE

U2 - 10.1016/j.tetlet.2011.01.010

DO - 10.1016/j.tetlet.2011.01.010

M3 - Article

SN - 0040-4039

VL - 52

SP - 1124

EP - 1127

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

Gold-mediated synthesis of alpha-ionone

Abstract

Keywords

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Projects

Molecular assembly using gold catalysis: Molecular assembly using gold catalysis

Cite this