A method for the stereoselective generation of 7,6- and 7,5-fused bicyclic lactams of type 1 has been developed. The key step involves intramolecular N-acyliminium ion cyclization of N-acyl enamine 2 to generate the core bicyclic framework. Lactams of type 1 may be viewed as conformationally restricted mimics of alanyl proline.