Journal of the American Chemical Society, Vol.120, No.1, 66-69, 1998
Chiral capsules. 1. Softballs with asymmetric surfaces bind camphor derivatives
Molecule-within-molecule complexes are proving ever more useful in physical organic chemistry. They provide means of stabilizing reactive intermediates,(1) observing new forms of stereoisomerism,(2) and accelerating certain reactions.(3) Although a number of chiral cavitands and complexes have been made,(4-8) and guests inside these have been expected to experience intensified sensations of asymmetry as a result of cramped quarters, the stereochemical features in these microenvironments remain largely unexplored. The possibilities range from asymmetric outer surfaces through asymmetric cavity Linings to asymmetric cavities. We now have them all in hand and introduce here the initial molecules with asymmetric surfaces. In the sequel, we will trace the gradual shift of research focus from the outside to the inside of the self-assembling "softball" 1.1.