Hemicryptophane Cages with a C 1 -Symmetric Cyclotriveratrylene Unit
Résumé
Two new hemicryptophanes combining a cyclotriveratrylene unit with either an aminotrisamide or a tris(2aminoethyl)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.
Domaines
ChimieOrigine | Fichiers produits par l'(les) auteur(s) |
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