About the Seminar:
Two Short Stories: (1) Developing a versatile contrathermal Cope rearrangement platform for enantioselective synthesis. (2) Toward atropselecitve disubstitution of nitroarenes.
The Cope Rearrangement is a classic transformation of value to organic synthesis. Certain substrates classes have been well developed due to their ready availability and generally favorable energetic profiles. Conversely, 3,3-dicyano-1,5-dienes have been overlooked. We have been exploring 3,3-dicyano-1,5-dienes and have uncovered strategies to improve their energetic profiles in general ways that impact their applicability to complex molecule synthesis. This first half of this seminar will focus on how the marriage of theory and experiment has impacted Cope rearrangement-centered strategies for enantioselective synthesis.
The second portion of the talk will focus on the development of a new strategy for achieving atropselecitve disubstitution of nitroarenes. The linking of carbon-based functional groups and (hetero)aromatics to (hetero)arene building blocks is critical considering the prominence of this pattern in pharmaceuticals. Modern strategies that achieve this in rapid fashion include metal-catalyzed cross-coupling, directed C–H functionalization, the Catellani reaction, aryne chemistry, and many photocatalysis transformations. New methods that achieve this goal and yield access to complementary, complex (functional, structural, and three-dimensional complexity) chemical space is essential to the drug discovery pipeline. Disclosed at this seminar will be the the development of cine-ipso-disubstitution of nitroarenes: a versatile strategy toward complex, functionally-dense, axially chiral biaryl motifs.
About the Speaker:
Alex is from the northern suburbs of Chicago. He received his B.A. degree from Lake Forest College under the research supervision of Dr. William B. Martin in 2007. He received his Ph.D. in Chemistry in 2012 from the University of Kansas under the guidance of Prof. Jon A. Tunge where he developed various decarboxylative and deacylative allylation reactions. In 2012, he moved to Boston University to work with Prof. John A. Porco on complex molecule synthesis, most notably the development of new routes to polyprenylatedacylphloroglucinol (PPAP) natural products and analogs. Alex’s independent career began in the summer of 2014 when he joined the faculty in the Department of Chemistry at the University of Florida in Gainesville. He was promoted to Associate Professor in 2021.
The Grenning Lab’s research goals are to simplify complex molecule synthesis through the invention of novel chemical methodologies and strategies and to discover natural product-inspired chemotherapeutics. Some of their research goals are supported through the NIH (R35 GM137893-01; 2020 – 2025) and the NSF (CAREER 1844443; 2019 – 2024).
Other interests include rock n’ roll, a good beer or cocktail with friends, longboarding, biking, swimming, and packin’ up the truck for a long weekend camping trip.
