The focus of this research is to develop new synthetic methodology for stereoselective [3+2] reactions based on Lewis-acid promoted ylide formation for the preparation of complex heterocycles. The project will focus on carbonyl oxides and azomethine ylids produced by conrotatory 4-pi ring opening of epoxides and aziridines in the presence of Lewis acidic metals and enantiomerically pure ligand systems. Applications will include the synthesis of non-racemic mixtures of diols and the synthesis of (-)-kainic acid. The focus of the educational effort will be the introduction of team-based learning approaches to chemistry. Dr. Johnson has delineated new approaches for the education of advanced organic students at U.N.C.
With this CAREER award, the Organic and Macromolecular Chemistry Program is supporting the research and educational efforts of Dr. Jeffrey S. Johnson of the Department of Chemistry at the University of North Carolina, Chapel Hill. Professor Johnson will focus his research on the development of new methods for the construction of complex molecules that have potential for broader impact in the pharmaceutical industry. This work focuses on obtaining only one enantiomer (chiral isomer) of an organic compound where the potential for the formation of two isomers exists. These new methods could have important implications for the design of medicinally important compounds. The educational activity of the award revolves around improved ways to teach organic chemistry to undergraduates.