A novel palladium-catalyzed [4 + 1] cycloaddition to give spirotetrahydrofuran oxindoles has been developed, in which diphenyl 2-oxoindolin-3-yl phosphates were used as the both electrophilic and nucleophilic C1 synthons at C-3 of the oxindole unit and 2-methylidenetrimethylene carbonate was used as the 1,4-dipole. The cycloannulation was performed at room temperature and provided the corresponding spirotetrahydrofuran oxindoles in good to excellent yields. The present method affords a new strategy for the construction of spirooxindole derivatives with unique three-dimensional structures.