The focus of this research is the use of boronic esters in asymmetric synthesis. New chemistry which should be useful for convergent syntheses will be studied, including a new type of allylic group transfer from one boron atom to another, and connection of halo boronic esters to carboxylic ester enolates. Both of these yield a new chiral center at the connection point, potentially with high stereoselectivity. Cyclization of halo boronic esters will be used for making four- and five-membered rings with chirality control. Intramolecular Diels-Alder reactions using vinyl boron intermediates will be investigated. A mild method of generating alkoxyborohydrides, discovered in the Principal Investigator's laboratory, will be utilized as a route to new and inexpensive asymmetric reducing agents. %%% With this Renewal award, the Synthetic Organic 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 the use of boronic esters in asymmetric synthesis as a general method for the production of chiral molecules.
