Synthesis of substituted conformationally constrained 6,5- and 7,5-fused bicyclic lactams as dipeptide mimics

Using a convenient and practical route we report the preparation of a series of rigid surrogates of amino acids and dipeptides for application within constrained peptide analogues, and for employment as input for combinatorial science. These substituted 2-oxo-1-azabicycloalkane amino acids have the potential of replicating the backbone geometry and side-chain function of dipeptide residues like serine, lysine, glutamate, and related amino acids.