Virtual Lecture Series:
Frontiers in Synthetic and Medicinal Chemistry

Exploiting the Versatile N-O Bond: Synthesis of Amines and N-heterocycles
Prof. László Kürti
Department of Chemistry
Rice University
Houston, TX

Pharmaron’s Virtual Lecture Series provides online educational training for our team and partners during the COVID-19 pandemic. World-class scientists from renowned academic institutions present their latest novel research on topics related to synthetic and medicinal chemistry.

Synthesis of highly substituted and strained nitrogenous molecules remains a challenging task since  installing substituents on small ring systems gets increasingly difficult as the degree of  substitution increases. Similarly, it is difficult to install nitrogen bridges onto highly substituted and electronically diverse unsaturated systems. In this lecture, Professor Kürti will discuss a number of synthetic routes to these valuable nitrogenous building blocks: (1) The direct and stereospecific synthesis of N-H- and N-alkyl aziridines from unactivated olefins using both transition metal-catalyzed and organocatalytic approaches that proceed through very different N-transfer processes; (2) Fully-substituted N-acyl aziridines are produced in one-pot by the reaction of N-electrophilic iminomalonates with ketone enolates - this transformation is in essence an aza-quasi-Favorskii rearrangement reaction which proceeds via a 1,2-attack followed by a low-barrier intramolecular nitrenoid-insertion into a C-C bond and (3) Structurally diverse spiro N-H azetidines are formed in a single step during the Ti(IV)-mediated reaction between oxime ethers and alkyl-Grignard reagents or via a ligand-exchange process using terminal olefins - the overall transformation proceeds via a Kulinkovich-type mechanism: a titanacyclopropane intermediate is formed and serves as a 1,2- dialkyl anion equivalent, inserting into the 1,2-dielectrophilc oxime ether to ultimately give rise to the desired N-heterocyclic four-membered ring.

About Prof. László Kürti:

Prof. László Kürti was born and raised in Hungary. He received his Diploma from Lajos Kossuth University (now University of Debrecen) where he conducted research in the laboratory of Prof. Sándor Antus focusing on the total synthesis of benzofuranoid neolignans. Subsequently he received his Master of Science degree at the University of Missouri-Columbia, working with Prof. Michael Harmata on inter- and intramolecular [4+3]-cycloadditions of halogen-substituted oxoallylic cations, and his Ph.D. degree (2006) in synthetic organic chemistry under the supervision of Prof. Amos B. Smith III at the University of Pennsylvania where he developed a new method for the construction of highly substituted and strained indoles that was applied in the synthetic studies toward the construction of the complex indole diterpenoid natural products, nodulisporic acids A and B.

In 2006, Prof. Kürti joined the group of Prof. E. J. Corey at Harvard University as a Damon Runyon Cancer Fellow where he was working on the development of potent antiangiogenic agents inspired by the structure of Cortistatin A. In 2007 he co-authored the book Molecules and Medicine with Prof. E. J. Corey and Dr. Barbara Czakó. In February 2008, the Professional and Scholarly Division of the American Association of Publishers designated Molecules and Medicine “Best of Physical Sciences and Mathematics”. In the Fall of 2010, Prof. Kürti and Prof. Corey self-published “Enantioselective Chemical Synthesis: Methods, Logic and Practice” that was warmly received by the community. Now this book is sold by Elsevier/Academic Press.

Prof. Kürti began his independent career as an Assistant Professor in the Department of Biochemistry at UT Southwestern Medical Center, Dallas, Texas, but on June 1, 2015, he joined the faculty at Rice University (Houston, Texas) as an Associate Professor in the Department of Chemistry. He was promoted to the rank of Full Professor on July 1, 2021. His laboratory is located in the BioScience Research Collaborative (BRC) building that has state of the facilities and offers many opportunities for collaborations.

This presentation will take place on Thursday, June 30, 2022, 9:00 am (China Standard Time) / Wednesday, June 29, 2022, 8:00 pm (Central Time). To join, complete the form below and you'll receive the login and password.

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