The enantioselective oxidative cyclizations of gamma-alkenyl arylsulfonamides and a delta-alkenyl arylsulfonamide for the synthesis of nitrogen heterocycles are presented. The reactions are catalyzed by chiral copper(II) complexes, and MnO2 is used as the inexpensive stoichiometric oxidant. A variety of five-membered heterocycles and a tetrahydroisoquinoline have been synthesized in good to excellent yields with good to excellent levels of enantioselectivity. This is the first reported copper-catalyzed enantioselective carboamination of alkenes.