A general method for the alpha-acyloxylation of carbonyl compounds

Autor: Niall M. Killeen, Teyrnon C. Jones, Nicholas C. O. Tomkinson, Adrian Hall, Paul H. Taylor, Kerri L. Jones, Cory S. Beshara, Robert J. Jenkins, Stephen P. Thomas
Rok vydání: 2005
Předmět:
Zdroj: Organic letters. 7(25)
ISSN: 1523-7060
Popis: [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.
Databáze: OpenAIRE