The focus of this research is the development of catalysts for the asymmetric phosphonylation of aldehydes to form alpha-hydroxyphosphonamides of high optical purity. In addition, allylic hydroxyphosphonates will be prepared and the methodology will be applied to the preparation of enzyme inhibitors. With this award, the Synthetic Organic Program is supporting the research of Dr. Christopher D. Spilling of the Department of Chemistry at the University of Missouri, St. Louis. Professor Spilling will focus his work on the development of synthetic methodology for the preparation of alpha-hydroxyphosphonamides, a class of compounds having important biological activity.