Remote Control of Helical Chirality: ThermodynamicResolution of a Racemic Mixture of CTV Units by Remote StereogenicCenters.

Enantiopurehemicryptophanes designed from the cyclotriveratrylene(CTV) unit display remarkable properties in selective host–guestrecognition or as supramolecular catalysts. The unprecedented controlof the helical chirality of the CTV unit by remote stereogenic centersof a tren moiety is reported, providing an original access to thishighly promising class of host molecules. Although the chiral centersand the CTV unit are separated by more than 10 Å, one singlediastereomer is formed; the nature of the diastereoselective processis discussed and the procedure is exemplified using different enantiopuretren derivatives. This work also highlights the influence of the chiralityof the CTV unit on the whole cage structure. [ABSTRACT FROM AUTHOR]