A general procedure for the synthesis of enones via gold-catalyzed Meyer-Schuster rearrangement of propargylic alcohols at room temperature

Matthew N Pennell; Matthew G Unthank; Peter Turner; Tom D Sheppard

doi:10.1021/jo102263t

A general procedure for the synthesis of enones via gold-catalyzed Meyer-Schuster rearrangement of propargylic alcohols at room temperature

J Org Chem. 2011 Mar 4;76(5):1479-82. doi: 10.1021/jo102263t. Epub 2011 Jan 25.

Authors

Matthew N Pennell¹, Matthew G Unthank, Peter Turner, Tom D Sheppard

Affiliation

¹ Department of Chemistry, University College London, Christopher Ingold Laboratories, 20, Gordon Street, London WC1H 0AJ, UK.

PMID: 21265538
DOI: 10.1021/jo102263t

Abstract

Meyer-Schuster rearrangements of propargylic alcohols take place readily at room temperature in toluene with 1-2 mol % PPh(3)AuNTf(2), in the presence of 0.2 equiv of 4-methoxyphenylboronic acid or 1 equiv of methanol. Good to excellent yields of enones can be obtained from secondary and tertiary alcohols, with high selectivity for the E-alkene in most cases. A one-pot procedure for the conversion of primary propargylic alcohols into β-arylketones was also developed, via Meyer-Schuster rearrangement followed by Pd-catalayzed addition of a boronic acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Catalysis
Gold / chemistry*
Ketones / chemical synthesis*
Ketones / chemistry
Molecular Structure
Propanols / chemistry*
Stereoisomerism
Temperature*

Substances

Alkynes
Ketones
Propanols
Gold
propargyl alcohol