To verify our designed strategy, we began our study by mixing easily accessible methyleneindolinone 1a with 3-bromo-1nitropropane (2a), bifunctional organocatalysts, and base (Table ). To our delight, a reaction conducted with commercially available Takemoto catalyst (C1) and K2CO3 produced spirooxindole derivative 3a as the main diastereomer. Moreover, compound 3a was readily separable on silica and isolated in good yield (58%) with high enantioselectivity (99% ee, entry 1). Besides, we observed the formation of 5a in traces as a product of base-induced HNO2 elimination. Conversely, the diastereocontrol of the reactions catalyzed by Rawal´s and Soos´s catalysts was significantly diminished (entries 2 and 3). Apart from C1-C3, we tested other bifunctional organocatalysts (for details, please see the SI file), but no further improvement in reaction efficiency was observed. Interestingly, the reaction rate was significantly decreased when using Na2CO3 (entry 4) and NaHCO3 (entry 5). Using organic bases, such as DIPEA (entry 6), significantly reduced diastereocontrol. Then, the effect of solvent on reaction efficiency and the stereochemical outcome was evaluated. Using polar aprotic solvents (ethyl acetate or MTBE) resulted in the highest reaction rates. On the other hand, diastereoselectivities of those reactions were significantly lowered (entries 7 and 8). The model reaction conducted in chloroform (entry 8) produced spirooxindole 3a in high yield, with excellent stereochemical outcome. Additionally, we conducted the model reaction with reduced amount of 3-bromo-1-nitropropane (2a) and organocatalyst C1 (1 mol%), producing 3a with the same efficiency and stereocontrol (entry 11). For complete optimization studies, please, see the SI.