This research project by R. Pagni and G. Kabalka of the University of Tennessee is within the Organic Dynamics Program, and is aimed at an understanding of organic reactions on surfaces. Most of our knowledge about organic reactions comes from experiments run in the liquid or gas phase. It is expected that reactions which occur on solid surfaces might take a different course, and this will provide new fundamental information about reaction pathways and also provide new opportunities for organic synthesis. Two synthetic reactions will be examined on solid surfaces: asymmetric induction in Diels-Alder reactions and macrocycli- zation. Asymmetric induction reactions have been studied widely in solution, but rarely on surfaces. Surfaces have attractive features for these reactions provided that the surface is chiral. This can be achieved by using surfaces that are intrinsically chiral or which are made chiral by adsorption of chiral molecules. Macrocyclization, the synthesis of large rings from acyclic precursors, is a long-standing problem when performed in solution. For carefully selected cases this reaction should be easily achieved on solids because competing intermolecular side reactions will be inhibited.
