In summary, we have developed enantioselective organocascade Michael/spirocyclization reaction of readily available methyleneindolinone with 1-bromo-3-nitropropane. The reaction is efficiently catalyzed by a chiral bifuncitional catalyst, affording chiral spirooxindole-fused cyclopentanes in moderate-to-good yields and excellent stereochemical outcomes. The developed synthetic protocol is suitable for late-stage functionalizations, as shown by a set of additional transformations.