A practical, effective, and regionselective palladium-catalyzed ring opening/[4+2] annulation of enaminones with cyclopropenones for the controllable synthesis of highly substituted γ-butenolides and γ-lactams have been described. This method for the first time regio-selective annulation reaction on the carbon and amine groups of the enaminone structure. This reaction characterized by its wide substrate scope, good functional group compatibility, moderate to good yields, scale-up synthesis, and versatile transformations, providing a versatile and general protocol to construct γ-butenolides and γ-lactams.