Herein, we report a practical two‐step synthetic route to α‐arylpyrrolidines through Suzuki–Miyaura cross‐coupling and enantioselective copper‐catalyzed intramolecular hydroamination reactions. The excellent stereoselectivity and broad scope for the transformation of substrates with pharmaceutically relevant heteroarenes render this method a practical and versatile approach for pyrrolidine synthesis. Additionally, this intramolecular hydroamination strategy facilitates the asymmetric synthesis of tetrahydroisoquinolines and medium‐ring dibenzo‐fused nitrogen heterocycles. An enantioselective copper‐catalyzed intramolecular hydroamination reaction can be used jointly with the Suzuki–Miyaura cross‐coupling to yield a diverse array of α‐arylpyrrolidine scaffolds that contain pharmaceutically relevant heteroarenes with excellent enantiomeric purity under mild conditions. Furthermore, this intramolecular hydroamination strategy is applicable to the asymmetric syntheses of six‐ to nine‐membered benzo‐fused nitrogen heterocycles.