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A general method for the α-acyloxylation of carbonyl compounds

Beshara, Cory S. and Hall, Adrian and Jenkins, Robert L. and Jones, Kerri L. and Jones, Teyrnon C. and Killeen, Niall M. and Taylor, Paul H. and Thomas, Stephen P. and Tomkinson, Nicholas C. O. (2005) A general method for the α-acyloxylation of carbonyl compounds. Organic Letters, 7 (25). pp. 5729-5732. ISSN 1523-7060

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Abstract

A simple, one-pot method for the α-acyloxylation of carbonyl compds. that proceeded at room temp. 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 provided the α-functionalized product in good isolated yield. The transformation was tolerant of a wide range of functional groups and, significantly, was regiospecific in the discrimination of secondary over primary centers in the case of nonsym. substrates.