Chemistry Lecture: Recent Developments in the Exploitation of Pd-Catalyzed b-Hydride Eliminations

The Department of Chemistry and Biochemistry in the J. William Fulbright College of Arts and Sciences will host a presentation, "Recent Developments in the Exploitation of Pd-Catalyzed b-Hydride Eliminations," by Doug E. Frantz, Distinguished Professor in the Department of Chemistry at the University of Texas at San Antonio.

This lecture will be at 3:30 p.m. today, April 9, in Chemistry Building 114. Refreshments will follow in CHEM 105.

Abstract: Frantz's will discuss the methodology program in my group has a long-term goal of exploiting metal-mediated b-hydride eliminations as a powerful new approach in synthetic methodology and asymmetric catalysis. Our recent focus has been on the synthesis of allenes through a surprisingly facile b-hydride elimination from cationic vinyl Pd(II)-complexes. Perhaps more importantly, is our ultimate goal to continue to exploit catalytic asymmetric b-hydride eliminations as a novel process to establish axial chirality in allenes with high stereochemical fidelity. We believe that the shortage of complementary catalytic methodologies that can produce diverse arrays of chiral allenes in high enantiomeric purity has stymied the full reaction potential and limited the broad industrial application of the only common functional group in organic chemistry that possess axial chirality. An update on our latest findings in this area will be presented including a brief discussion on related catalytic methodologies and chemical biology programs ongoing in my group.

About Doug E. Frantz: He currently holds the Max and Minnie Tomerlin Distinguished Professorship in Chemistry at The University of Texas at San Antonio. He earned his Ph.D. in organic chemistry at Texas A&M University in 1998 with Dr. Dan Singleton where he studied the mechanistic details of organocuprate conjugate additions using natural abundance kinetic isotope effects (KIEs) and NMR techniques.  He then moved on to do a post-doctoral fellowship with Erick Carreira at the ETH Zürich in Zürich, Switzerland where he discovered and developed the Zn-catalyzed asymmetric acetylide additions to aldehydes resulting in 8 publications in 14 months. Frantz then joined the Process Research group at Merck & Co., in 2000 in Rahway, New Jersey, followed by a move to Wayne, Pennsylvania, to help start up a brand new site for Merck where he remained until 2005. While at Merck, he helped develop robust syntheses for several clinical candidates across a wide-range of therapeutic areas including diabetes, chronic pain, oncology, and neurodegeneration.  He decided to return to Texas in 2005 to pursue a career in academia where he joined the faculty in the Department of Biochemistry at the University of Texas Southwestern Medical Center at Dallas as a research assistant professor and Director of the Synthetic Chemistry Core Facility.

In 2009, he was recruited to the Department of Chemistry at UTSA where he has recruited outstanding colleagues in organic chemistry that has rapidly established the department as one of the premier places for organic chemistry in Texas.  His research group continues to pursue their mutual interests in asymmetric catalysis, physical organic chemistry, stem cell differentiation, and drug discovery.  He is also Co-Founder of the Center for Innovative Drug Discovery (CIDD), a joint drug discovery initiative between UTSA and the UT Health Science Center in San Antonio that has received over $12 million in funding since its inception.  Doug has received several awards including the Thieme Journal Award (2017), Lilly Open Innovation Drug Discovery Outstanding Collaborator Award (2014), and the Max and Minnie Tomerlin Young Investigator Award (2010).  He also served as Co-Chair of the GRC on Organic Reactions and Processes (2014) and has established the TexSyn conference in 2013 with Prof. Mike Krische at UT Austin to highlight the outstanding research in synthetic organic chemistry in the state of Texas every two years.