Closed vs Open-Shell CTV Based Host Compounds: A Direct Comparison
Résumé
New hemicryptophane compds. combining a cyclotriveratrylene (CTV) unit, three binaphthol moieties in the linkers and closed by a simple benzene unit have been synthesized enantiomerically and diastereomerically pure. Assignment of their abs. configuration was achieved by chem. correlation. These closed shell host compds. were then tested in the recognition of carbohydrates and compared with their open-shell counterparts. Closing the mol. cage induces a slight drop in affinity, assocd. with an improvement in the stereoselectivity of the recognition process, probably related to the higher preorganization of the cage compds.