In this project funded by the Chemical Synthesis program of the Chemistry Division, Professor Chiles W. Downey of the Department of Chemistry at the University of Richmond will explore the use of silylating agents for the acceleration, mediation, and catalysis of an array of chemical reactions. Silylating agents such as trimethylsilyl trifluoromethanesulfonate will act in two roles. First, the eletrophilic silicon center will act as a Lewis acid to activate other electrophiles toward nucleophilic attack. Second, the formation of strong silicon-oxygen or other silicon-heteroatom bonds will help drive these chemical reactions to completion, affording high yields and shorter reaction times. Of particular interest are alpha-substitution reactions of carboxylic acids, a class of reactions commonly hampered by strongly basic reaction conditions. When these reactants are employed, the silylating agent can play a third role by transforming the acid functional group into a more easily controllable silyl ester. This work could lead to the development of asymmetric reactions of carboxylic acids, such as an asymmetric carboxylic acid aldol reaction.
This project has significant impacts on fundamental biological sciences, pharmaceutical and agricultural industries, as it would provide direct access to chiral carboxylate building blocks important in the biosynthesis and chemical synthesis of complex molecules of potent biological activities. The emphasis upon one-pot reactivity reduces the generation of waste, providing a positive environmental impact as well as savings with respect to time and economics. The project also provides trainings for undergraduate research students in preparation for careers in the science health fields as well as academia. Over the course of this award, six to eight researchers will be funded for an intensive ten-week summer research experience in addition to experiments carried out during the regular academic year.
