A new modification of the Passerini reaction: a one-pot synthesis of α-acyloxyamides via sequential Kornblum oxidation/Passerini reaction

A novel approach for the synthesis of α-acyloxyamides is described. Benzylic substrates (halides or tosylates), under mild Kornblum conditions, are oxidized to give the corresponding aldehydes, which undergo a Passerini reaction with carboxylic acids and isocyanides to produce the corresponding α-acyloxyamides in excellent yields.