Cycloaddition yields spirocyclopentyl indanediones up to 95% in diverse solvents, suggesting efficient divergent synthesis pathways.
MgI₂-mediated formal (3 + 2) cycloaddition (ring-opening cyclization) and ring-opening iodination-Michael addition of spirocyclopropyl indanediones and nitroalkenes have been developed respectively in tetrahydrofuran and toluene, which constitutes an efficient protocol for the solvent-controlled divergent synthesis of spirocyclopentyl indandiones (up to 95% yield, >20:1 dr) and 2,2-disubstituted indanediones (up to 68% yield). Based on control experiments and a high-resolution mass spectrometry experiment, a plausible reaction mechanism has been proposed.
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Yang et al. (2025) studied this question.
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