Copper-catalyzed alkene diamination: synthesis of chiral 2-aminomethyl indolines and pyrrolidines

Chiral vicinal diamines, including 2-aminomethyl indolines and pyrrolidines, are useful as ligands for catalytic asymmetric reactions and are also found as important components of bioactive compounds. Herein is reported the first copper-catalyzed alkene diamination that occurs with high enantioselectivity. The substrate range is the broadest yet reported for this kind of intra-/intermolecular reaction sequence both with respect to γ-alkenyl sulfonamide substrate and external amine nucleophile. The resulting products expand the availability of substituted 2-aminomethyl indolines and pyrrolidines, privileged compounds in asymmetric catalysis and medicinal chemistry. A unique solution to a challenging oxidation problem related to copper catalyst turnover is also presented.