From?-lactams to?- and?-amino acid derived peptides

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Abstract
The potential ofβ-lactams as intermediates for the access toα- andβ-amino acid-derived peptides is shortly reviewed, with major focus on the technologies developed in our group. The two general strategies lie, on one side, in the oxidative ring expansion of 3-hydroxyβ-lactams toN-carboxyα-amino acid anhydrides or Leuch's anhydrides and subsequent coupling withα-amino acid esters and, on the other side, in the nucleophilic ring opening ofN-Boc-β-lactams. Both approaches have been successfully applied to the synthesis ofα,β-diamino acid,α-amino-β-hydroxy acid, polyhydroxylatedα-amino acid,α,α-disubstitutedα-amino acid,β-amino acid,β-amino-α-hydroxy acid andβ,β-disubstitutedβ-amino acid derived peptides. Because of the mild reaction conditions needed for the above transformations and the highly stereoselective procedures employed for the construction of the startingβ-lactam ring, the whole process allows the production of optically pure final products.

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