The Chemical Synthesis Program of the NSF Chemistry Division supports the research of Professor T. Andrew Mitchell in the Department of Chemistry at Illinois State University. Often referred to as the central science, chemistry continues to demonstrate extensive utility. Organic chemistry advances biology, medicine, physics, materials, economic development, national defense, and environmental sustainability. Professor Mitchell and his students study important bond-forming reactions called cycloadditions. These reactions perform a crucial function within the discipline of organic synthesis by enabling efficient and selective transformations of flat molecules to three-dimensional building blocks that are embedded within biologically active compounds. Although new reaction discoveries are intellectually fascinating, Dr. Mitchell is equally passionate about training next generation scientists to ask important questions within an organic chemistry CORE (Collaboration, Outreach, Research, Education) curriculum in preparation for the chemical workforce. Collaboration invites students in a research laboratory to work with a range of other scientists. Creativity, teamwork, presentation, deeper understanding, and characterization of new compounds are taught in this environment. For example, students learn to think on their feet and engage in nuanced scientific discussions during lab work and group meetings. Outreach provides opportunities for high school students, many from underrepresented groups, to participate in research experiences during the summer. Research in the undergraduate environment opens the door for greater sophistication through mentorship, critical reasoning, and exposure to state-of-the-art instrumentation as students take ownership of knowledge acquired in coursework. Education in the classroom includes guiding students toward confident inquiry while using various technological platforms to enhance content delivery.
The main intellectual merit objectives of this project are to expand the mechanistic understanding and the practical utility of silyloxypyrone-based [5+2] cycloadditions toward construction of otherwise inaccessible natural and unnatural heterocyclic scaffolds. The Mitchell research group utilizes kinetic isotope effects, linear free energy relationship studies based on the Hammett equation, and collaborative theoretical calculations to elucidate various mechanistic scenarios of silyloxypyrone-based [5+2] cycloadditions. These studies expand the knowledge of [5+2] cycloadditions and lead to new directions such as asymmetric induction, intermolecular variants, and others. Broader impacts illustrate the superb training ground of [5+2] cycloadditions for next generation scientists. Several activities are integrated with discovery through our CORE (Collaboration, Outreach, Research, Education) program. This research has potential impact on the US chemical industry.
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.
