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Helical, Axial, and Central Chirality Combined in a Single Cage: Synthesis, Absolute Configuration, and Recognition Properties
Author(s) -
Zhang Dawei,
Mulatier JeanChristophe,
Cochrane James Robert,
Guy Laure,
Gao Guohua,
Dutasta JeanPierre,
Martinez Alexandre
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600664
Subject(s) - enantiopure drug , chirality (physics) , absolute configuration , diastereomer , enantiomer , stereochemistry , chemistry , axial chirality , asymmetric carbon , enantioselective synthesis , crystallography , optically active , organic chemistry , physics , chiral symmetry , catalysis , quantum mechanics , quark , nambu–jona lasinio model
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.