This award will support a two-year U.S.-Japan cooperative science project between Professor Julius Rebek, Department of Chemistry, Massachusetts Institute of Technology, and Professor Kenji Koga, Faculty of Pharmaceutical Sciences, University of Tokyo. The project involves the investigation of catalytic proton transfer agents for asymmetric chemical synthesis. This cooperative effort seeks to develop the techniques and understanding of factors governing the stereoelectronics of protonation and deprotonation. This will require a focus on both the proton source as well as the trajectory of proton transfer. Professor Rebek has performed extensive studies of stereoelectronic effects at carboxyl function and the chemistry of molecular recognition. Professor Koga has a program in asymmetric deprotonation reactions and the chemistry of lithiated amine bases. Their collaboration in this project draws on the complementarity of their research programs.