Inherently chiral phosphonatocavitands as artificial chemo- and enantio-selective receptors of natural ammoniums

Jérôme Vachon (1) , Steven Harthong (1) , Erwann Jeanneau , Christophe Aronica (1) , Nicolas Vanthuyne (2) , Christian Roussel (2) , Jean-Pierre Dutasta (1)

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

Inherently chiral phosphonatocavitands with various bridging moieties at their wide rim were synthesized. Optical resolution by chiral HPLC was performed with cavitand 8 to afford enantiopure compounds (+)-8 and (−)-8. The molecular structures of hosts 8 and 12 were determined by X-ray diffraction. The host properties were investigated by 1H and 31P NMR spectroscopy. The phosphonatocavitands form inclusion complexes with chiral ammonium neurotransmitters, some presenting enantioselectivity towards the right or left-handed host enantiomers.

Domaines: Chimie théorique et/ou physique

Jérôme Vachon, Steven Harthong, Erwann Jeanneau, Christophe Aronica, Nicolas Vanthuyne, et al.. Inherently chiral phosphonatocavitands as artificial chemo- and enantio-selective receptors of natural ammoniums. Organic & Biomolecular Chemistry, 2011, 9 (14), pp.5086-5091. ⟨10.1039/c1ob05194f⟩. ⟨hal-01116903⟩