A general procedure for the synthesis of enones via gold-catalyzed Meyer-Schuster rearrangement of propargylic alcohols at room temperature |
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| Authors: | Pennell Matthew N Unthank Matthew G Turner Peter Sheppard Tom D |
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| Institution: | Department of Chemistry, University College London, Christopher Ingold Laboratories, 20, Gordon Street, London WC1H 0AJ, UK. |
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| 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. |
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