Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides

A suite of flexible and chemoselective methods for the transition-metal-free oxidation of amides to alpha-keto amides and alpha-hydroxy amides is presented. These highly valuable motifs are accessed in good to excellent yields and stereoselectivities with high functional group tolerance. The utility of the method is showcased by the formal synthesis of a potent histone deacetylase inhibitor.