New synthesis of alpha-amino acid N-carboxy anhydrides through Baeyer-Villiger oxidation of alpha-keto beta-lactams

A novel method was developed to synthesize alpha-amino acid N-carboxy anhydrides (NCA), which were optically active, and their corresponding alpha-amino acid derivatives. The synthesis involved a Baeyer-Villiger rearrangement subsequent to alpha-hydroxy beta-lactam oxidation to the correlating alpha-keto beta-lactams. This reaction methodology facilitated the preparation of various NCAs from non-amino acid precursors.