We report the first catalytic, enantioselective reductive bis-functionalization of common amides, which provides a facile access to a variety of 2,2-disubstituted 3-iminoindolines in good yields and with excellent enantioselectivities. The reaction conditions are quite mild and can be run on a gram scale. In this one-pot reaction, three C-C bonds, one ring, and one nitrogen-containing tetrasubstituted carbon stereocenter are created in a catalytic enantioselective manner.