Abstract
Gold-catalyzed stereoselective synthesis of spirocyclopropyl oxindoles from diazooxindoles and 1,2,4-substituted dienes is described. The aim of this work is to report a novel rearrangement of these spirocyclopropyl oxindoles with a gold catalyst to yield 3-(cyclopenta-1,3-dien-1-ylmethyl)oxindoles. Our experimental data exclude a reversible process in the gold-catalyzed cyclopropanation. With DFT calculations, we postulate a rearrangement mechanism involving the formation of complex pairs of gold enolates and 1-methylen-2,3,4-cyclopentadienyl cations, leading to a 1,5-enolate shift.
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