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The enantioselective vinylogous Mannich reaction of ketimines derived from isatins with acyclic vinylketene silyl acetals has been developed using a chiral bis(imidazoline)-Cu(II) catalyst. A series of chiral 3-aminooxindole derivatives bearing tetra-substituted stereogenic centers with an α,β-unsaturated ester moiety were obtained in excellent yields (up to 99%) with high enantioselectivities (up to 98% ee). Enantioselective bisvinylogous Mannich reaction to ketimines derived from isatins also afforded product with high enantioselectivi