Ligand Scaffold Optimization for Catalytic Asymmetric Hydroboration

University Of Nebraska-Lincoln, Lincoln NE

Investigators

Abstract

This project will continue work on the development of chiral self-assembled ligands and catalysts for the catalytic asymmetric hydroboration of alkenes. Chirality-directed self-assembly enables the rapid in situ preparation of dozens, even hundreds, of unique ligand scaffolds and thus permits the subtle structural manipulation of catalyst topography in ways not available with classical ligand designs. While stoichiometric asymmetric hydroboration is widely used, the catalyzed reaction is underdeveloped relative to its potential utility in asymmetric synthesis. Combinatorial type screening of chiral self-assembled ligands will be carried out to identify new useful supramolecular catalysts. Studies to further elucidate the reasons for the success of these catalysts will be undertaken to provide new fundamental insight into asymmetric catalysis. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Takacs of the Department of Chemistry at the University of Nebraska-Lincoln. Professor Takacs? research efforts revolve around the development of supramolecular catalysts using self-assembly to generate macromolecular scaffolds that define the shape and characteristics required for efficient catalysis, an approach that mimics biological catalysts. This application focuses on the formation of synthetically useful and versatile C-B bonds via metal-catalyzed hydroboration, a reaction that holds significant untapped potential for asymmetric synthesis. Such chemistry holds the promise to replace a stoichiometric reaction protocol with a catalytic one and thus contribute to environmentally benign methods for chemical synthesis. Successful development of the methodology will have an impact on synthesis in the pharmaceutical and agricultural industries.