Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various types of optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities (84-98% ee). This is realized by the use of the cationic iridium complex [Ir(cod)₂](BAr(F)₄) and the chiral O-linked bidentate phosphoramidite (R,R)-Me-BIPAM.