With this renewal proposal the Organic and Macromolecular Chemistry Program supports the work of Dr. Michael P. Doyle at the University of Arizona. The work builds on earlier results using asymmetric metal carbene transformations for intramolecular cyclopropanation and C-H insertion using chiral dirhodium(II) carboxamidate complexes to synthesize organic compounds difficult to make by other means. He plans to increase the reactivity of the dirhodium catalysts by modifying the carboxamidate ligands, investigate double diastereoselection, carry out asymmetric ylide transformations, produce macrocyclic compounds with rings of up to 20 atoms, and determine the importance of ligand steric and electronic factors in determining catalyst yields and selectivities.
This work involves fundamental research in improved ways to synthesize chiral organic compounds using homogeneous catalysts with chiral ligands. The methods are likely to be useful in the synthesis of pharmaceuticals and agricultural chemicals. Dr. Doyle has helped to train 23 undergraduate students in the past five years, in a unique arrangement in which they work with postdoctoral students in Dr. Doyle's laboratory.
