A general method for the alpha-acyloxylation of carbonyl compounds.
[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.
Beshara
Cory S
CS
School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff CF10 3AT, UK.
Hall
Adrian
A
Jenkins
Robert L
RL
Jones
Kerri L
KL
Jones
Teyrnon C
TC
Killeen
Niall M
NM
Taylor
Paul H
PH
Thomas
Stephen P
SP
Tomkinson
Nicholas C O
NC