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Abstract A highly efficient and direct approach was developed to construct the structurally diverse spirooxindole skeleton, which is an important basic motif in natural products. Both the 3,3′-pyrrolidonyl spirooxindoles and spiroindolin-2-one δ-lactones were smoothly obtained by the intramolecular Dieckmann cyclization of oxindoles in excellent yield under mild conditions. Graphical Abstract