Confronting Challenges in Regiocontrol By Means of Dienolates and Strained Rings

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

About the Speaker

Justin Mohr was born and raised in Anchorage, AK. He received his A. B. from Dartmouth College in 2003. During his time at Dartmouth, he conducted research aimed at elucidating the molecular mechanism of anesthesia as a Beckman Scholar in the laboratory of Prof. Gordon Gribble. Justin pursued graduate research with Prof. Brian Stoltz at the California Institute of Technology where he developed enantioselective palladium-catalyzed enolate reactions. In 2009, Justin joined Prof. Gregory Fu's laboratory at the Massachusetts Institute of Technology as a National Institute of Health Ruth L. Kirschstein Postdoctoral Fellow. While at MIT, Justin explored the synthesis and use of aza-b-lactams as selective inhibitors of serine hydrolase enzymes in collaboration with Prof. Benjamin Cravatt's laboratory at The Scripps Research Institute. In 2012 Justin joined the faculty at the University of Illinois at Chicago as an Assistant Professor. His research interests include development of new reaction methodology, organometallic chemistry, and the synthesis of bioactive molecules.