Support is provided by the Organic Synthesis Program to continue Professor Donald S. Matteson's studies of asymmetric synthesis with boronic esters in the Department of Chemistry at Washington State University. Professor Matteson will examine the cyclization of asymmetric boronic esters to obtain chiral cyclobutanes, providing a new route for the synthesis of natural products, typified by the boll weevil pheremone, grandisol. Reactions allowing the conversion of boronic esters to alkyldihaloboranes will be developed, and these reactions will be modified through intramolecular delivery of nucleophilic centers to afford new syntheses of nitrogen- and oxygen-containing heterocycles. Catalytic chirality control in the formation of carbon-carbon bonds will be assayed, as will reactions resulting in the conversion of carbon-boron bonds to carbon-nitrogen and carbon-carbon bonds. These studies will open the doors for the preparation of C2-chiral diamines and the study of retroracemization reactions, allowing complete conversion of racemic boronic ester substrates to a single diastereomeric product. Many molecules exist which bear the same relationship to their mirror image as a right hand bears to a left hand - they look the same, but they are not identical. Often, one form of a molecule will display different properties, particularly with regards to biological activity, than those of its mirror image form, and thus synthetic organic chemists must devise methods for the preparation of single forms of desired molecules. Professor Matteson will explore such `asymmetric` syntheses by developing the chemistry of compounds containing boron, exploiting the unusual chemical reactivity of such compounds to facilitate the formation of new carbon-carbon and carbon-nitrogen bonds. He will develop routes to broad classes of compounds, providing a general foundation on which to build the field of asymmetric synthesis, and also will highlight the practical utility of the chemistry through the synthesis of a molecule which may serve as an agent for the control of boll weevil infestations.
