Enantioselective copper-catalyzed cyclization of gamma-alkenylsulfonamides and a delta-alkenylsulfonamide in the presence of a range of vinyl arenes results in variously functionalized 2-substituted chiral nitrogen heterocycles via a formal alkene C-H functionalization process. Application of this reaction to the concise synthesis of a 5-HT7 receptor antagonist is demonstrated.