title: Helical, Axial, and Central Chirality Combined in a Single Cage: Synthesis, Absolute Configuration, and Recognition Properties.
abstract: The synthesis of eight enantiopure molecular cages (four diastereomeric pairs of enantiomers) comprising a helically chiral cyclotriveratrylene (CTV) unit, three axially chiral binaphthol linkages, and three centrally asymmetric carbon atoms of a trialkanolamine core, is described. These new cages constitute a novel family of hemicryptophanes, which combine three classes of chirality. Their absolute configuration was successfully assigned by a chemical correlation method to overcome the signals overlap in the ECD spectra of the binaphtol and CTV units. Stereoselective recognition of glucose and mannose derivatives was investigated with these new chiral cages. Excellent enantio- and diastereoselectivity were reached, since in some cases, both exclusive enantio- and diastereo-discrimination have been observed. In addition, compared with the most relevant hemicryptophanes, these new cages also exhibit improved binding affinities.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P. R. China.|Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, UCBL, 46 allée d'Italie, 69364, Lyon, France.
authors.forename: Dawei
authors.initials: D
authors.lastname: Zhang
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, UCBL, 46 allée d'Italie, 69364, Lyon, France.
authors.forename: Jean-Christophe
authors.initials: JC
authors.lastname: Mulatier
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, UCBL, 46 allée d'Italie, 69364, Lyon, France.
authors.forename: James Robert
authors.initials: JR
authors.lastname: Cochrane
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, UCBL, 46 allée d'Italie, 69364, Lyon, France. laure.guy@ens-lyon.fr.
authors.forename: Laure
authors.initials: L
authors.lastname: Guy
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P. R. China. ghgao@chem.ecnu.edu.cn.
authors.forename: Guohua
authors.initials: G
authors.lastname: Gao
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, UCBL, 46 allée d'Italie, 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, 69364, Lyon, France. alexandre.martinez@ens-lyon.fr.|Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France. alexandre.martinez@ens-lyon.fr.
authors.forename: Alexandre
authors.identifier: http://orcid.org/0000-0002-6745-5734
authors.initials: A
authors.lastname: Martinez
keywords: carbohydrates; chirality; hemicryptophane; molecular cages; stereoselective recognition