title: Cyclotriveratrylene-BINOL-Based Host Compounds: Synthesis, Absolute Configuration Assignment, and Recognition Properties.
abstract: New host compounds combining a cyclotriveratrylene (CTV) unit and three binaphthol moieties have been synthesized enantiomerically and diastereomerically pure. The use of a chemical correlation allows for the assignment of their absolute configuration. The energy barrier of epimerization was measured, suggesting that no intramolecular hydrogen bonding occurs between the hydroxyl groups of the binaphthols. These open-shell host compounds were then tested in the recognition of carbohydrates; a preferential binding of mannose toward glucose was observed, and good diastereoselectivities were reached (up to 1:10). This recognition of sugar derivatives by open-shell CTV-based host compounds is unprecedented and opens up the way for a wider use of this easily accessible class of molecules as chiral sensors.
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon , CNRS, UCBL 46, Allée d'Italie, F-69364 Lyon, France.
authors.forename: Sara
authors.initials: S
authors.lastname: Lefevre
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon , CNRS, UCBL 46, Allée d'Italie, F-69364 Lyon, France.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Héloin
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon , CNRS, UCBL 46, Allée d'Italie, F-69364 Lyon, France.
authors.forename: Delphine
authors.initials: D
authors.lastname: Pitrat
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon , CNRS, UCBL 46, Allée d'Italie, F-69364 Lyon, France.
authors.forename: Jean-Christophe
authors.initials: JC
authors.lastname: Mulatier
authors.affiliation: Aix Marseille Université , Centrale Marseille, CNRS, iSm2 UMR 7313, 13397 Marseille, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Vanthuyne
authors.affiliation: Aix Marseille Université , Centrale Marseille, CNRS, iSm2 UMR 7313, 13397 Marseille, France.
authors.forename: Marion
authors.initials: M
authors.lastname: Jean
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon , CNRS, UCBL 46, Allée d'Italie, F-69364 Lyon, France.
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Dutasta
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon , CNRS, UCBL 46, Allée d'Italie, F-69364 Lyon, France.
authors.forename: Laure
authors.initials: L
authors.lastname: Guy
authors.affiliation: Aix Marseille Université , Centrale Marseille, CNRS, iSm2 UMR 7313, 13397 Marseille, France.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Martinez