Asymmetric Synthesis with Boronic Esters

Washington State University, Pullman WA

Investigators

Abstract

The focus of this research is the development of asymmetric methods for synthesis using boronic acid chemistry. Conversion of boronic esters to stable alkyltrifluoroborates and then on to highly reactive alkyldihaloboranes will be used for the asymmetric synthesis of secondary amines and development of new carbon-carbon bond forming reactions. Catalysis involving an enantioenriched boronic acid as the catalyst and a dialkyl bifluoroborate salt as a trap for the reaction products will be explored. The ability to construct vicinal alkyl-bearing stereocenters, unique amine-bearing stereocenters, and highly functionalized four- and five-membered rings will be exploited in the total synthesis of representative natural products. With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Donald S. Matteson, of the Department of Chemistry at Washington State University. Professor Matteson will focus his work on developing asymmetric synthesis methodology using boronic ester chemistry. The area of research is excellent for the training of graduate students and the results of the research could have implications for the pharmaceutical and agricultural industries.