With the support of the Organic and Macromolecular Chemistry Program, Professor Scott R. Gilbertson, of the Department of Chemistry at Washington University, is studying the synthesis of P,N-based ligands for application in catalytic asymmetric reactions. Professor Gilbertson is developing synthetic routes for new phosphine-oxazoline ligands which are chiral at phosphorus and position the phosphorus at the bridgehead of a [2.2.1] bicyclic ring system. In order to expand the range of accessible chiral ligands containing P-C bonds, Gilbertson explores the catalytic conversion of vinyl tosylates to vinylphosphines and thence to new ligands. New ligands are screened for their ability to assist in the catalysis of a mechanistically diverse range of reactions, including palladium catalyzed pi allyl addition, the Heck reaction, asymmetric hydroboration, and rhodium catalyzed [4+2] cycloisomerization.
Many of the organic compounds discovered to possess desirable properties (e.g., as pharmaceutical compounds) exist in two forms, related to one another as a right hand is to a left - i.e., as mirror images. Not infrequently, only one such isomer of a compound will display the desirable properties, while the other is at best an inactive contaminant and at worst displays harmful activity. The development of new techniques for the selective synthesis of only a desired compound and not its mirror image remains a crucial area for investigation. With the support of the Organic and Macromolecular Chemistry Program, Professor Scott R. Gilbertson, of the Department of Chemistry at Washington University, is developing novel classes of compounds designed to function, together with various metal ions, as catalysts for a variety of reactions affording such selectivity.
