α,β-unsaturated aldehydes and N-sulfonylimines undergo direct, N-heterocyclic carbene (NHC) catalyzed annulations to give enantioenriched cis-disubstituted lactams via the intermediacy of catalytically generated homoenolates. Critical to the success of this reaction is the use of novel chiral azolium salts as catalysts. The development, scope, mechanism, and extension of these studies to novel, enantioselective NHC-catalyzed annulations reactions will be reported.