1,4-dicarbonyls represent a frequently occurring substructure found in natural products that also serves as an integrant for the formation of cyclic compounds. The method explores the construction of these substructures through the use of oxyallyl cations. Recently oxyallyl cations have been reported to undergo functionalization into useful synthons through nucleophilic addition at the alpha carbon under a variety of conditions. This chemistry utilizes the inherent reactivity of the oxyallyl cation and mild conditions to exhibit a novel methodology useful in generating differentiated 1,4-dicarbonyls in a regioselective manner.

1,4-Dicarbonyl synthesis using oxyallyl cations

251st National Meeting (2016)

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