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

Jérôme Vachon; Steven Harthong; Erwann Jeanneau; Christophe Aronica; Nicolas Vanthuyne; Christian Roussel; Jean-Pierre Dutasta

doi:10.1039/C1OB05194F

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Organic & Biomolecular Chemistry

Issue 14, 2011

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

Jérôme Vachon , Steven Harthong , Erwann Jeanneau , Christophe Aronica , Nicolas Vanthuyne , Christian Roussel and Jean-Pierre Dutasta

Org. Biomol. Chem., 2011,9, 5086-5091

DOI: 10.1039/C1OB05194F
Received 04 Feb 2011, Accepted 14 Apr 2011
First published on the web 14 Apr 2011

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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.