CAREER: Metallooxaziridines for the Synthesis of Nitrogen-Containing Three-Membered Heterocycles

Rowan University, Glassboro NJ

Investigators

Abstract

The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Gustavo Moura-Letts. Professor Moura-Letts is a faculty member in the Department of Chemistry at Rowan University. He is developing new classes of chemical reagents for the synthesis of nitrogen-containing molecules. These nitrogen-containing molecules are important for the construction of medicinally relevant natural products and can be found in several approved drugs. In spite of their importance, there remains a significant need for the development of short and selective methods to make these nitrogen-containing drug molecules. The goal of this research is to exploit the unique chemical properties of specific metal complexes that allow for the construction of a wide variety of nitrogen-containing molecules in a fashion previously unexplored. This project is also developing mechanisms to engage undergraduates, high school students, and returning veterans in chemical research. The goal is to stimulate their interest in scientific careers. Metallooxaziridines are stable nitrogen-containing organometallic complexes that have the potential to efficiently promote the formation of three-membered ring heterocycles through the delivery of a nitrogen atom across pi-systems. To capitalize on this reactivity, three objectives are being pursued. 1) The reaction efficiency and scope of metallooxaziridine reactions with alkenes, aldehydes and imines for the synthesis of aziridines, oxaziridines and diaziridines respectively is being explored. 2) The reaction between pi-systems and metallooxaziridines are being studied in order to determine if the reactions can be run with using catalytic amount of the metal. 3) The potential for the reactions to be conducted in an asymmetric fashion are being investigated. In combination with these efforts, the work in connection with the educational plan is establishing a laboratory training system in which undergraduates and graduate students can receive a broad preparation in chemical synthesis along with research-training rotations in correlated areas of research. A plan to develop a science certificate program for returning Veterans is also being pursued in an effort to provide those individuals with a path to a productive career in the sciences. 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.