Abstract
A conceptually new route for the generation of optically active α-aminoacid N-carboxy anhydrides (NCAs) and hence α-amino acid derivatives is described. The strategy developed is simple and consists of the oxidation of α-hydroxy β-lactams to the corresponding α-keto β-lactams followed by a Baeyer-Villiger rearrangement. By that means, a wide variety of functionalized α-aminoacid N-carboxy anhydrides can be obtained, i.e., α,β-diamino acid and β-amino β-hydroxy acid-derived NCAs. The starting α-hydroxy(alkoxy) β-lactams required for the study are easily prepared in large quantities either by the cycloaddition reaction of achiral alkoxyketenes with chiral aldehyde-derived imines or by the addition of Grignard reagents to a 3-(benzyloxy)-4-formylazetidin-2-one. The construction of a wide variety of NCA's from non-amino acid precursors becomes the most remarkable point of the reaction methodology developed
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