Rh(I)-Catalyzed [3+2] annulation reactions of cyclopropenones with amides are reported. The reaction provides a direct approach for producing highly substituted α,β-unsaturated γ-lactam derivatives. The presence of an N(sp²) atom in the N-alkyl group of the amide, such as the 2-pyridinylmethyl or 8-aminoquinonyl group, is essential for the success of the reaction.