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

Research output: Contribution to journalArticlepeer-review

87 Citations (Scopus)

Abstract

Meyer-Schuster rearrangements of propargylic alcohols take place readily at room temperature in toluene with 1-2 mol % PPh3AuNTf2, 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.(Figure Presented)

Original languageEnglish
Pages (from-to)1479-1482
Number of pages4
JournalJournal of Organic Chemistry
Volume76
Issue number5
Early online date25 Jan 2011
DOIs
Publication statusPublished - 4 Mar 2011
Externally publishedYes

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