A General Method for the α-Acyloxylation of Carbonyl Compounds
Organic Letters2005Vol. 7(25), pp. 5729–5732
Citations Over TimeTop 17% of 2005 papers
Cory S. Beshara, Adrian Hall, Robert L. Jenkins, Kerri L. Jones, Teyrnon C. Jones, Niall M. Killeen, Paul H. Taylor, Stephen P. Thomas, Nicholas C. O. Tomkinson
Abstract
[chemical reaction: see text]. A simple, one-pot method for the alpha-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 alpha-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.
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