Electrophilic α-amination reaction of β-ketoesters using N -hydroxycarbamates: Merging aerobic oxidation and lewis acid catalysis

Abstract

The copper-catalyzed α-amination of carbonyl compounds using nitrosoformate intermediates as the electrophilic source of nitrogen is reported. The reaction merges aerobic oxidation and Lewis acid catalysis. The scope of the reaction is broad in terms of both the N-substituted hydroxylamines and the β-ketoesters. The new methodology harnesses the power of nitrosoformate intermediates and demonstrates their potential as a viable electrophilic source of nitrogen in α-functionalization reactions. © 2012 American Chemical Society.