In our group, we recently developed organocatalyzed and base mediated C3 functionalization of isatylidene malononitriles to synthesize different spirooxindoles. Continuing with this vision, this time we aim to synthesize the 3,3'-pyrrolidonyl spirooxindole scaffold. Wang et al. have reported a methodology for the synthesis of spirooxindole via reductionlactamization Cascade. In this strategy, the selective reduction of the nitro group of nitro-Michael adduct by ferrous sulphate to an amine is followed by spontaneous lactamization to yield the product. In a plausible mechanism, the amine attacks the ester group of nitro-Michael adduct to synthesize spirooxindole (Scheme 1 a). Particularly noteworthy in our methodology it was observed selective attack of hydroxylamine on the nitrile group, resulting the formation of a single diastereomeric highly functionalized 3,3'-pyrrolidinyl-spirooxindole (Scheme 1 b).