Amidation of Enones via Beckmann Rearrangement.

The Beckmann reaction is one of the most atom-economical methods for the preparation of amides from ketones. Unlike ketones, the multiple competing reactivities of enones as well as the requirement of demanding reaction conditions for in situ generation of oximes have severely impacted the application of this reaction for the preparation of α,β-unsaturated amides. Herein, we describe the first chemoselective method for the direct conversion of enones to the corresponding α,β-unsaturated amides using -Boc--tosylhydroxylamine.