title: Remote control of helical chirality: thermodynamic resolution of a racemic mixture of CTV units by remote stereogenic centers.
abstract: Enantiopure hemicryptophanes designed from the cyclotriveratrylene (CTV) unit display remarkable properties in selective host-guest recognition or as supramolecular catalysts. The unprecedented control of the helical chirality of the CTV unit by remote stereogenic centers of a tren moiety is reported, providing an original access to this highly promising class of host molecules. Although the chiral centers and the CTV unit are separated by more than 10 Å, one single diastereomer is formed; the nature of the diastereoselective process is discussed and the procedure is exemplified using different enantiopure tren derivatives. This work also highlights the influence of the chirality of the CTV unit on the whole cage structure.
authors: Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, UCBL , 46, Allée d'Italie, F-69364 Lyon, France.
authors: Bastien
authors: B
authors: Chatelet
authors: Lionel
authors: L
authors: Joucla
authors: Daniele
authors: D
authors: Padula
authors: Lorenzo
authors: L
authors: Di Bari
authors: Guillaume
authors: G
authors: Pilet
authors: Vincent
authors: V
authors: Robert
authors: Véronique
authors: V
authors: Dufaud
authors: Jean-Pierre
authors: JP
authors: Dutasta
authors: Alexandre
authors: A
authors: Martinez
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D011083:Polycyclic Compounds; C483859:cyclotriveratrylene