CAREER: Chiral Catalysts for Enantioselective Photoredox-Catalyzed Carbon-Carbon Bond-Forming Reactions

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In this project, funded by the Chemical Catalysis program of the NSF Chemistry Division, Professor Ming-Yu Ngai of the Department of Chemistry at Stony Brook University develops new and efficient photochemical reactions to prepare chiral organic molecules. Chiral molecules exist in specific configurations known as enantiomers. Each configuration has the same atoms, but arranged spatial in a different order, this results in different chemical properties. The goal of this project is to design and optimize novel catalysts to yield specific enantiomers. It is often important to select one specific enantiomer because the other is ineffective or harmful. New synthetic methods developed in this research may have applications in the syntheses of pharmaceuticals, agrochemicals, and materials chemistry. An integral part of this program is to recruit and prepare a diverse STEM (Science, Technology, Engineering and Mathematics) workforce to advance the frontiers of science. This project provides students with opportunities for industrial training through collaboration with a major pharmaceutical company. Professor Ngai establishes a hands-on synthetic module to introduce organic synthesis and molecular photochemistry to high school students and a summer industrial internship program to better prepare graduate students for future careers in advanced chemical manufacturing.Over half of all top-selling drugs are marketed as single enantiomers; often because the other enantiomer is ineffective or harmful. As a consequence, catalytic reactions that can readily increase the structural complexity of molecules while maintaining control of the stereochemistry of the newly formed stereocenters are of importance in drug discovery and development. Visible-light photoredox catalysis has emerged as a potentially powerful tool in organic synthesis. This catalysis has changed the way in which chemists approach some difficult synthetic problems. Precise stereocontrol of photocatalytic reactions remains a significant challenge. This research focuses on the design and development of chiral Lewis acid catalysts which enable stereoselective, visible-light mediated photoredox catalysis. These new catalysts are applied to enantioselective cross-coupling reactions of carbonyl and iminyl derivatives with alkenes. This project generates a library of novel tridentate chiral ligands and chiral catalysts that guide the development of asymmetric chemical transformations. The hands-on organic synthesis activities developed by Professor Ngai enrich the educational experience of high school students and encourage them to pursue advanced degrees in STEM (Science, Technology, Engineering and Mathematics) education. These activities also provide training opportunities to pre-service chemistry teachers for their professional development. An established industrial collaboration and a summer internship program for graduate students at Boehringer Ingelheim further support career development in advanced chemical manufacturing.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.