A New Versatile Synthesis of Oxazoles by Intramolecular Aza-Wittig Reaction

Article abstract of DOI:10.1021/jo00263a033

A new synthesis of oxazoles by an intramolecular aza-Wittig reaction is described.Readily available α-azido ketones 2 were converted to (Z)-β-(acyloxy)vinyl azides 3 by selective enol acylation.These vinyl azides 3 reacted with triethyl phosphite to afford the corresponding oxazole derivatives 5 via the Staudinger reaction, followed by an intramolecular aza-Wittig reaction.In particular, this oxazole synthesis was useful for oxazoles having acid-labile substituents.