An efficient asymmetric synthesis of oxindole‐pyrazolone adducts via organocatalytic Mannich reaction of 1‐phenyl‐1H‐pyrazol‐5(4H)‐ones with ketimine derivatives derived from isatins, followed by sequential electrophilic fluorination, has been developed. This approach offers a facile way to prepare chiral 3‐amino‐3‐(4‐fluoropyrazol‐4‐yl)‐substituted oxindole derivatives with a wide range of functional group tolerance.