Abstract
Abstract The reaction of cross-conjugated dienolate anions derived from substituted cyclohexenones with methyl acrylate and vinyl ketones has been studied. Bicyclo[2.2.2]octan-2-ones are formed by a sequential Michael mechanism; however, the reactions of vinyl ketones must be conducted under amine-free conditions. Unexpecedly, the conjugate base from 2,3-dimethylcyclohex-2-enone gives only a single Michael adduct with vinyl ketones, and if forced to react further undergoes an intramolecular aldol condensation. An alternative Diels-Alder approach to the bicyclo[2.2.2]octanone products is shown to be effective.
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