Organic Chemistry Seminar (Justin Mohr, University of Illinois at Chicago)

May 8, 2017 at - | Lynch Lecture Hall Chemistry Complex



Title:  Regio- and Stereocontrol with Anions and Radicals




Dienolates and their synthetic equivalents provide a versatile platform for regioselective functionalization protocols owing to their ambident reactivity.  Exploration of radical additions to these synthons is examined as a potential solution to the problem of γ-functionalization of cyclic ketones.  In addition, anioinic dienolates are studied as unusual regiodivergent branch points for the synthesis of halogenated arenes from common, readily available precursors.  Aspects of regio- and stereoselectivity are important components that provide mechanistic insights into these transformations.  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 are underway.