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Wednesday, February 19, 2020
4:00 PM - 5:00 PM
Noyes 153 (J. Holmes Sturdivant Lecture Hall)

Organic Chemistry Seminar

Universal Alkene Functionalization as an Aspirational Driver
Keary M. Engle, Professor, Department of Chemistry, Scripps Research Institute,
Speaker's Bio:
Keary graduated Phi Beta Kappa and summa cum laude from the University of Michigan, where he carried out research with Prof. Adam J. Matzger. During undergrad, he spent one summer with Prof. A. Stephen K. Hashmi at the University of Stuttgart as a DAAD RISE Fellow, and then spent the year after graduation performing research with Prof. Manfred T. Reetz at the Max-Planck-Institut für Kohlenforschung as a Fulbright Scholar and with Prof. Jan E. Bäckvall at Stockholm University as an IDECAT Exchange Fellow. He completed his graduate work jointly at The Scripps Research Institute with Prof. Jin-Quan Yu and the University of Oxford with Profs. Véronique Gouverneur and John M. Brown, earning a PhD in Chemistry and a DPhil in Biochemistry. During grad school, he also carried out summer research with Prof. Kyoko Nozaki at the University of Tokyo as an NSF/JSPS EASPI Fellow. After completing a two-year appointment as an NIH Postdoctoral Fellow with Prof. Robert H. Grubbs at Caltech, Keary joined the faculty at The Scripps Research Institute in the summer of 2015. His research interests lie at the interface of organometallic chemistry, organic synthesis, and catalysis. Outside of the lab, Keary enjoys running long distances, eating fried chicken, drinking good beer, and spending time with his wife and dog.

Vicinal (1,2-disubstituted) functional group motifs are ubiquitous in structurally complex small molecules that are of academic and industrial importance, including many widely used pharmaceutical agents. Many such functional group combinations, however, remain exceptionally challenging to synthesize. The goal of research in the Engle lab is to develop a general catalytic platform for alkene and alkyne difunctionalization to introduce a diverse array of functional groups at each of the two carbon atoms in a programmable fashion. Our central hypothesis is that is that Lewis basic directing groups can be used to: (1) control the regioselectivity of Heck- and Wacker-type alkene addition, (2) stabilize the resultant alkylmetal intermediate to allow to allow efficient downstream trapping, and (3) enhance selectivity for three-component coupling over competitive two-component coupling. This concept has been used to expand the synthetic toolkit to include new retrosynthetic disconnections, including “homo-Michael” addition and β,γ-vicinal dicarbofunctionalization of alkenyl carbonyl compounds.

For more information, please contact Rena Becerra Rasti by phone at 626-395-6151 or by email at rasti@caltech.edu.