An efficient and facile one-pot, multi-component reaction for the regio- and diastereoselective synthesis of novel dispirocyclopentanebisoxindoles has been reported by a reaction between phenyl-2-(triphenylphosphoranylidene)ethanone and isatin derivatives. The great advantages of this synthetic protocol are the minimal reaction steps, short reaction time, and operational simplicity. In consequence, a variety of new dispirocyclopentanebisoxindole derivatives with potential medicinal applications were synthesized through one-pot and multi-component reaction in high to excellent yields.