Diastereodivergent Catalysis with Modularly Designed Organocatalysts

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The Chemical Catalysis Program of the Chemistry Division supports the project by Professor John Zhao. Professor Zhao is a faculty member in the Department of Chemistry at the University of Texas at San Antonio (UTSA). He is developing a new method for the selective synthesis of multiple stereoisomers of organic molecules. Stereoisomers, which differ only subtly in their structures, may have totally different biological and/or pharmacological properties. The goal of this research project is to exploit the unique properties of modularly designed organocatalysts (MDOs) to achieve the easy synthesis of multiple diastereomers of complex organic molecules from the same starting materials, which is presently a very challenging task in chemistry. The research greatly facilitates the exploration of new chemical space and drug discovery. This project offers research opportunities for students, including students from underrepresented minorities, who are preparing for careers in the chemical sciences. UTSA is one of the most diverse institutions of higher education in the United States. Professor Zhao's group provides a high level of education and training for students through a variety of outreach programs that are already in place at UTSA.Catalytic asymmetric syntheses of multiple diastereomers of various important polysubstituted carbocyclic and heterocyclic compounds are under investigation. The researchers use the same starting materials and different modularly designed organocatalysts to selectively generate different stereoisomers of the targets. Specifically, Professor Zhao is pursuing the development of novel MDO catalysts that are self-assembled from readily available precatalysts and the utilization of the MDOs in the catalytic tandem reactions for the diastereodivergent synthesis of polysubstituted carbocyclic and heterocyclic compounds. The method is being investigated for the diastereodivergent syntheses of bioactive natural products of medicinal relevance. The research provides new catalysts that not only achieve the divergent synthesis of different stereoisomers of important molecules, but also improves the stereoselectivity in the synthesis. Stereoselective synthesis is a current challenge in asymmetric catalysis. The research results are being incorporated into an organic laboratory aimed at undergraduates to help stimulate their interest and attract these students to the chemical sciences.