Synthesis of azabicycloalkane amino acid scaffolds as reverse-turn inducer dipeptide mimics

In an effort to design dipeptide structural mimics of protein and peptide reverse-turns, a series of 5,5-, 6,5-, and 7,5-fused 2-oxo-1-azabicycloalkane amino acids has been synthesized. A new and convenient synthetic route utilizing a Homer-Emmons reaction followed by double-bond reduction has been used to prepare the bicyclic lactams in high yields.