Abstract
α-Hydroxy-β-dicarbonyls are known to undergo base-induced rearrangement to α-acyloxy carbonyls by a mechanism believed to involve an oxirane C–C bond scission step. Herein, we report the first example of this process in a vinylogous system. An attempt to access the protected form of the putative oxirane intermediate revealed an additional rearrangement pathway that was available to the substrate. Oxirane C–C bond cleavage mechanisms were invoked to explain both isomerizations.
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