2015 Beckman Symposium   

Justin Mohr, PhD

Presentation Date:
August-8-2014

Presenter:
Justin Mohr, PhD

Title:
Regioselective Reactions of Dienolates: Expedient Synthesis of Substituted Arenes and Heterocycles

Institution:
University of Illinois, Chicago

Department:
Chemistry

Description:

Our goal is to facilitate the chemical synthesis of particular molecular structures by developing more efficient transformations and strategies that complement existing methods.  One of the most important recent methods has employed palladium metal complexes as catalysts for forming carbon-carbon bonds.  These so-called cross-coupling transformations are useful for the synthesis of pharmaceuticals, agrochemicals, and polymers.  The Nobel Prize in Chemistry was awarded for this chemistry in 2010.  In general, these transformation rely on some pre-functionalization of the starting molecule, usually with a halogen atom.  A hindrance to the overall efficiency of cross-coupling reactions is the sometimes challenging synthesis of these halogen-containing substrate molecules.  We have chosen to address the synthesis of such compounds using a particular synthetic strategy that allows for efficienct control of precisely where that necessary halogen atom is incorporated into the structure of the molecule.  This is a significant advantage because many of the classical methods for introducing a halogen will lead to mixtures of structures with the same chemical formula, but a different specific arrangement of the atoms.  Separating the isomers is often very difficult.  We have found that we can use a single feedstock compound and by varying our reaction conditions we can directly access either of two isomeric products in high yield, thereby enabling the synthesis of diverse chemical structures.  All of this technology improves the scope and applications of the Nobel Prize-winning palladium chemistry.  We have been able to apply some of the palladium-catalyzed reactions to show some of the derivative chemical structures that we can make, and we anticipate using these transformations to explore bioactive molecules that contain these substructures.

 BIO:

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-beta-lactams as 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.

 


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