Bicyclic aziridines possessing a 1-azabicyclo[4.1.0]heptan-2-one core were prepared from 2 H-azirines by a stepwise annulation sequence involving a diastereoselective allylindanation, an N-acylation, and a ring-closing metathesis to construct the six-membered ring. After hydrogenation or functionalization of the olefin, regioselective ring opening of the resulting azabicyclic compounds with carboxylic acids (or sulfur nucleophiles) afforded highly substituted azepanones possessing an ester moiety or a trifluoromethyl group and a tetrasubstituted carbon at the α and β positions of the nitrogen atom, respectively.