Enantiopure C 1 -Cyclotriveratrylene with a Reversed Spatial Arrangement of the Substituents

Augustin Long (1) , Cédric Colomban (1) , Marion Jean (1) , Muriel Albalat (1) , Nicolas Vanthuyne (1) , Michel Giorgi (2) , Lorenzo Di Bari (3) , Marcin Górecki (4) , Jean-Pierre Dutasta (5) , Alexandre Martinez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 AMU SPEC - Spectropôle - Aix Marseille Université
3 University of Pisa - Università di Pisa
4 Institute of Organic Chemistry [Warsaw]
5 LC - Laboratoire de Chimie - UMR5182

Cyclotriveratrylene (CTV) is a macrocyclic cyclophane presenting a bowl-shaped conformation, used as building block to construct cryptophane and hemi-cryptophane 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.

Domaines: Chimie organique

Augustin Long, Cédric Colomban, Marion Jean, Muriel Albalat, Nicolas Vanthuyne, et al.. Enantiopure C 1 -Cyclotriveratrylene with a Reversed Spatial Arrangement of the Substituents. Organic Letters, 2019, 21 (1), pp.160-165. ⟨10.1021/acs.orglett.8b03621⟩. ⟨hal-02098280⟩