Chiral Dirhodium(II) Catalysts for Carbenoid Transformations

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With support from the Organic Dynamics Program, Dr. Doyle will design new chiral rhodium catalysts that will be used to generate carbenoids from diazocompounds. Intramolecular cyclization reactions of these carbenoids that lead, e.g., to the formation of lactones and lactams are expected to display exceptionally high enantioselectivities. It is likely that significant new, synthetically useful methods for asymmetric synthesis will result from this work. The reactions to be studied include chiral intra- and inter- molecular cyclopropanations, cycloadditions to aromatic systems, and carbon-hydrogen insertion processes that result in the formation of lactones and lactams. These studies will consist of a combination of: (i) catalyst preparation and characterization, (ii) mechanistic investigations, and (iii) synthetic applications.