A facile and efficient one-pot rongalite-mediated self-dimerization of 3-acylidene-2-oxindoles has been developed for the diastereoselective synthesis of highly functionalized dispirocyclopentanebisoxindoles. The reaction proceeds via a domino sequence involving intermolecular Michael addition followed by intramolecular aldol cyclization under basic conditions. Rongalite, an inexpensive and readily available reagent (~$0.03/g), plays a crucial role in promoting the transformation, offering significant advantages such as operational simplicity, step economy, use of a green solvent system, scalability to gram-scale synthesis, and potential for post-functionalization. This methodology provides an efficient route to structurally complex oxindole frameworks with high stereocontrol, demonstrating broad synthetic utility.

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