Hemicryptophane Cages with a C 1 -Symmetric Cyclotriveratrylene Unit

Chunyang Li (1) , Anne-Doriane Manick (1) , Marion Jean (1) , Muriel Albalat (1) , Nicolas Vanthuyne (1) , Jean-Pierre Dutasta (2) , Xavier Bugaut (1) , Bastien Chatelet (1) , Alexandre Martinez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 LC - Laboratoire de Chimie - UMR5182

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: Chimie

Chunyang Li, Anne-Doriane Manick, Marion Jean, Muriel Albalat, Nicolas Vanthuyne, et al.. Hemicryptophane Cages with a C 1 -Symmetric Cyclotriveratrylene Unit. Journal of Organic Chemistry, 2021, 86 (21), pp.15055-15062. ⟨10.1021/acs.joc.1c01731⟩. ⟨hal-03516854⟩