Open AccessHemicryptophane Cages with a C1-Symmetric Cyclotriveratrylene Unit
Author(s) -
Chunyang Li,
AnneDoriane Manick,
Marion Jean,
Muriel Albalat,
Nicolas Vanthuyne,
JeanPierre Dutasta,
Xavier Bugaut,
Bastien Châtelet,
Alexandre Martinez
Publication year - 2021
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.1c01731
Subject(s) - chemistry , enantiopure drug , moiety , crystallography , stereochemistry , amine gas treating , cyclophane , symmetry (geometry) , regioselectivity , crystal structure , organic chemistry , catalysis , enantioselective synthesis , geometry , mathematics
Two new hemicryptophanes combining a cyclotriveratrylene unit with either an aminotrisamide or a tris(2-aminoethyl)amine (tren) moiety have been synthesized. Although a conventional synthesis approach was used, the molecular cages obtained are devoid of the expected C 3 symmetry. NMR analyses and X-ray crystal structure determination showed that these hemicryptophanes exhibited C 1 symmetry due to the unusual arrangement of the substituents of the cyclotriveratrylene unit. This unprecedented arrangement is related to a change in the regioselectivity of the Friedel-Crafts reactions that led to the CTV cap. This constitutes an original approach to access enantiopure chiral molecular cages with low symmetry.
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