Protic Acid Catalysis of Organic Reactions

Vanderbilt University, Nashville TN

Investigators

Abstract

This project will continue work on the development of new reactions catalyzed by protic acids to form carbon-carbon and carbon-heteroatom (nitrogen and/or oxygen) bonds. An emphasis is placed on the identification and development of functional groups (e.g. diazo alkanes and azides) that can be activated toward carbon-carbon bond formation by protic acids without protonative self-decomposition. Inspection of the mechanism of these reactions will yield a fundamental understanding of reactivity, and in so doing, provide a framework for broader conceptual application and development. The development of diastereoselective variations of these reactions will be an emphasis of this phase, leading ultimately to their application in the synthesis of complex contiguous aminopolyols. These studies continually expand the availability of stereochemically dense small molecules, such as aziridines and beta-amino acids, and particularly new chemical entities that can be transformed into common pharmacophores or used as a basis for new materials. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Jeffrey N. Johnston of the Department of Chemistry at Vanderbilt University. Professor Johnston's research efforts revolve around the development of novel stereoselective methods to form C-C and C-heteroatom (N/O) bonds. This research will result in greener chemical methods to more rapidly and efficiently prepare chiral small molecules. Successful development of the methodology will have an impact on synthesis in the pharmaceutical and agricultural industries.