3-Substituted-3-aminooxindoles have attracted the attention of organic and medicinal chemists because these motifs constitute the core structure of a number of natural products and drug candidates. The catalytic potential of chiral organocatalysts and metal catalysts has been successfully exploited for the synthesis of enantioenriched 3-amino-2-oxindoles via the addition of various nucleophiles to isatin imines. This review focuses on the catalytic asymmetric synthesis of chiral 3-amino-3-substituted-2-oxindoles.