Open AccessEnantiopure C1-Cyclotriveratrylene with a Reversed Spatial Arrangement of the Substituents
Author(s) -
A.M. Long,
Cédric Colomban,
Marion Jean,
Muriel Albalat,
Nicolas Vanthuyne,
Michel Giorgi,
Lorenzo Di Bari,
Marcin Górecki,
JeanPierre Dutasta,
Alexandre Martinez
Publication year - 2018
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.8b03621
Subject(s) - enantiopure drug , chemistry , cyclophane , modularity (biology) , stereochemistry , block (permutation group theory) , absolute configuration , spectroscopy , computational chemistry , molecule , organic chemistry , mathematics , combinatorics , biology , quantum mechanics , enantioselective synthesis , catalysis , physics , genetics
Cyclotriveratrylene (CTV) is a macrocyclic cyclophane presenting a bowl-shaped conformation, used as building block to construct cryptophane and hemicryptophane capsules. A method to synthesize new enantiopure CTV derivatives with an unprecedented spatial arrangement of their substituents, exhibiting C 1 symmetry, is described. The absolute configuration was assigned by ECD spectroscopy coupled with modeling. A statistical model has allowed for optimization of the proportion of C 1 CTV, and the modularity of this approach is also highlighted.
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