In this proposal we intend to combine recent discoveries concerning molecular shape with developments of stereoelectronic theory to generate synthetic catalyst. Specifically, molecular clefts, in which functional groups are arranged in a convergent senses, are expected to provide unique microenvironments for concerted catalysis of some fundamental organic reactions. These include enolization of ketones, hemiacetal cleavage and carbonyl addition reactions. Ultimately, binding forces between catalyst and substrate will be engineered into these systems to explore the suitability of these new molecular scaffolds as artifical enzymes.
