Synthesis, resolution, and chiroptical properties of hemicryptophane cage controlling the chirality of propeller arrangement of a C 3 triamide unit

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

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 AMU SPEC - Spectropôle - Aix Marseille Université
3 Institute of Organic Chemistry Polish Academy of Sciences
4 LC - Laboratoire de Chimie - UMR5182

The five-steps synthesis of a hemicryptophane cage combining a benzene-1,3,5-tricarboxamide unit and a cyclotriveratrylene (CTV) moiety is described. Chiral high-performance liquid chromatography (HPLC) was used to resolve the racemic mixture. The absolute configuration of the isolated enantiomers was assigned by comparison of the experimental electronic circular dichroism (ECD) spectra with the calculated ones. X-ray molecular structures reveal that the capped benzene-1,3,5-tricarboxamide unit adopts a structurally chiral conformation in solid state: the chirality of CTV moiety controls the Λ or Δ orientation of the three amides.

Mots clés: cyclotriveratrylene; enantiopure cages; absolute configuration; chiral HPLC; chirality of triamide units

Domaines: Chimie organique

Augustin Long, Marion Jean, Muriel Albalat, Nicolas Vanthuyne, Michel Giorgi, et al.. Synthesis, resolution, and chiroptical properties of hemicryptophane cage controlling the chirality of propeller arrangement of a C 3 triamide unit. Chirality, 2019, 31 (11), pp.910-916. ⟨10.1002/chir.23131⟩. ⟨hal-02514499⟩