A simple method for the alpha-oxygenation of aldehydes

Chem Commun (Camb). 2005 Mar 21:(11):1478-80. doi: 10.1039/b418101h. Epub 2005 Jan 24.


A mild, efficient and general method for the chemospecific alpha-oxygenation of aldehydes is described. Treatment of a series of aldehydes with N-tert-butyl-O-benzoyl hydroxylamine hydrochloride gives the corresponding alpha-oxygenated carbonyl via a proposed pericyclic rearrangement process.