We report the synthesis of gold-(I) complexes supported by imidazo-[1,5-a]-pyridine-based ligands featuring chiral aniline moieties at N(2). The synthesis is short, efficient, and modular, allowing for precise control over the steric and electronic properties of the coordination sphere of the metal. The design of these atypical chiral ligands was validated in the Au-(I)-catalyzed enantioselective intramolecular hydrocarboxylation of allenes, which furnished tricyclic N(1)-C(2)-fused oxazino-indolones in high yield and unprecedented levels of enantiocontrol.