Brønsted base-catalyzed α-oxygenation of carbonyl compounds utilizing the [1,2]-phospha-Brook rearrangement

Abstract

A novel α-oxygenation reaction of carbonyl compounds was developed by utilizing the [1,2]-phospha-Brook rearrangement under Brønsted base catalysis. The reaction proceeds via the oxidation of enolates followed by the [1,2]-phospha-Brook rearrangement to afford α-oxygenated ester derivatives from easily accessible substrates having high functional group tolerance. In addition, the atom-economical tandem reaction of α-diethylphosphono ester derivatives with oxaziridines, which involves a carbon–carbon forming process in addition to α-oxygenation, was established under the low temperature conditions.