A General Method for the α-Acyloxylation of Carbonyl Compounds

A simple, one-pot method for the α-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides th...

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Bibliographic Details
Published in:Organic letters 2005-12, Vol.7 (25), p.5729-5732
Main Authors: Beshara, Cory S, Hall, Adrian, Jenkins, Robert L, Jones, Kerri L, Jones, Teyrnon C, Killeen, Niall M, Taylor, Paul H, Thomas, Stephen P, Tomkinson, Nicholas C. O
Format: Article
Language:English
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Summary:A simple, one-pot method for the α-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides the α-functionalized product in 69−92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is regiospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052474e