Catalytic regio- and enantioselective hydroamination of less activated internal alkenes presents a challenge to synthetic chemists due to their low reactivity and the difficulty in simultaneously controlling regio- and enantioselectivities. Here, we report an iridium-catalyzed enantioselective hydroamination of internal alkenes directed by an amide. The amide group on the alkene effectively directs the catalyst to overcome the low reactivity and control the regioselectivity and the enantiotopic face selection. Phthalimide serves as the amination agent, which could be readily removed to afford a primary amine. This coordination assistance enables hydroamination to occur selectively at the remote position with up to 97 % ee, delivering valuable enantio-enriched γ-amino acid derivatives that are otherwise challenging to access.