Enantiopure encaged Verkade's superbases: Synthesis, chiroptical properties, and use as chiral derivatizing agent

Jian Yang (1) , Bastien Chatelet (1) , Damien Hérault (1) , Véronique Dufaud , Vincent Robert , Stephane Grass (2) , Jérôme Lacour (2) , Nicolas Vanthuyne (1) , Marion Jean (1) , Muriel Albalat (1) , Jean-Pierre Dutasta (3) , Alexandre Martinez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 Département de chimie physique [Genève]
3 LC - Laboratoire de Chimie - UMR5182

Verkade's superbases, entrapped in the cavity of enantiopure hemicryptophane cages, have been synthesized with enantiomeric excess (ee) superior to 98%. Their absolute configuration has been determined by using electronic circular dichroism (ECD) spectroscopy. These enantiopure encaged superbases turned out to be efficient chiral derivatizing agents for chiral azides, underlining that the chirality of the cycloveratrylene (CTV) macrocycle induces different magnetic and chemical environments around the phosphazide functions.

Keywords: chiral derivatizing agent; ECD; enantiopure cages; Verkade's superbase

Domains: Chemical Sciences

Jian Yang, Bastien Chatelet, Damien Hérault, Véronique Dufaud, Vincent Robert, et al.. Enantiopure encaged Verkade's superbases: Synthesis, chiroptical properties, and use as chiral derivatizing agent. Chirality, 2020, 32 (2), pp.139-146. ⟨10.1002/chir.23156⟩. ⟨hal-02611880⟩