Amide and Amine Nucleophiles in Polar Radical Crossover Cycloadditions: Synthesis of γ-Lactams and Pyrrolidines

In this work we present a direct catalytic synthesis of gamma-lactams and pyrrolidines from alkenes and activated unsaturated amides or protected unsaturated amines, respectively. Using a mesityl acridinium single electron photooxidant and a thiophenol cocatalyst under irradiation, we are able to directly forge these important classes of heterocycles with complete regiocontrol.