With this award, the Synthetic Organic Program will support the research of Dr. Gary A. Molander of the Department of Chemistry at the University of Colorado. Dr. Molander's research focuses on the area of stereoselective synthesis. Methodology involving neighboring group participation, the use of optically active organometallics and utilization of chiral epoxides form the basis of the proposed studies. Dr. Molander will center his efforts on three areas of stereoselective organic synthesis. First, Dr. Molander will strive to develop a general method for achieving 1,4- and 1,5-relative asymmetric induction in the addition of carbon nucleophiles to prochiral electrophilic centers. In a second area, he will generate chiral organometallics using thermodynamic equilibration of an internally complexed organomagnesium. In a third, he will probe unique uses of enantiomerically enriched oxiranes in organic synthesis. Several methods for regio- and stereocontrolled ring opening reactions of oxiranes are proposed, all of which constitute useful routs to enantiomerically enriched organic molecules.