An enantioselective domino reaction of 4-bromo-3-oxobutanoates with isatin-derived ketimines was developed to construct 3-amino-2-oxindoles with a quaternary stereocentre. In the presence of 1 mol-% of a bifunctional squaramide organocatalyst, the desired products were achieved in high yields (90-97 %) and with excellent enantioselectivities (92-99 % ee).