- A general method for the alpha-acyloxylation of carbonyl compounds.
A general method for the alpha-acyloxylation of carbonyl compounds.
Organic letters (2005-12-03)
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
PMID16321033
摘要
[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.