Dienolates and their synthetic equivalents provide a versatile platform for regioselective functionalization reactions owing to their ambident reactivity.  We have explored radical additions to these synthons as a potential solution to the problem of γ-functionalization of cyclic ketones and their congeners.  In addition, we have examined dienolates as an unusual regiodivergent branch point for the synthesis of halogenated arenes and related derivatives from common, readily available precursors.  In separate studies, selective scission of carbon–carbon bonds is investigated using ring strain as a directing element and activating effect.  Applications of these strategies in target-directed synthesis efforts have been explored.

Regio- and stereocontrol with anions and radicals

256th National Meeting (2018)

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