Nitrosocarbonyl–Henry and Denitration Cascade: Synthesis of α‑Ketoamides and α‑Keto Oximes

An
unprecedented Henry reaction of in situ generated nitrosocarbonyl
intermediates and concomitant denitration cascade has been developed.
The reaction is catalyzed by organic base at room temperature offering
α-ketoamides, a demanding scaffold for drug discovery, in high
yields. An alteration of substitution pattern also produced α-keto
oximes, a high-value synthon. The protocol features operational simplicity
and broad substrate scope.