The spirooxindole system is one of the most important classes of naturally occurring substances with highly pronounced biological properties and is also the core structure of many synthetic pharmaticeuticals.These potential properties have prompted many efforts toward the synthesis of various spirooxindole derivatives.1 Recently, we successfully developed an practical synthetic protocol for dispirocyclopentyl-3,3-bisoxindoles with two oxindoles at 1,2-position of cyclopentyl ring by cycloaddition reaction ofp-dimethylamino-N-alkoxycarbonylmethylpyridinium salts with two molecular 3-methyleneoxindole derivatives.2 In order to further develop the synthetic values of this protocol,we investigated the base promoted reaction 3-phenacylideneoxindoles with nitromethane.The domino reaction of nitromethane with molecular 3-phenacylideneoxindoles in refluxing ethanol in the presence of DBU afforded fimctionalized dispirocyclopentyl-3,3-bisoxindoles with two oxindole units at 1,2-positions of the newly formed cyclopentyl ring in good yields and with high diastereoselectivity.On the other hand, a mixture of two diastereoisomers of dispirocycloperltyl-3,3-bisoxindoles with two oxindole units at 1,3-positions were also obtained in lower yields when the reactions were carried out in DMF with KF-Al2O3 as base.