The synthesis of sterically congested amides was accomplished via Cp*Co(III)-catalyzed sequential C–H bond addition to 1,3-dienes followed by aminocarbonylation with isocyanates, a coupling partner that had never been utilized in sequential C–H bond addition reactions. A variety of C–H bond reactants, internally substituted dienes, and aromatic isocyanates provided secondary amide products incorporating α-all-carbon quaternary centers. The conversion of the amide products to other useful compound classes was also demonstrated.