The absolute configuration of an inherently chiral phosphonatocavitand and its use toward the enantioselective recognition of l-adrenaline - Aix-Marseille Université Accéder directement au contenu
Article Dans Une Revue Tetrahedron: Asymmetry Année : 2010

The absolute configuration of an inherently chiral phosphonatocavitand and its use toward the enantioselective recognition of l-adrenaline

Résumé

An inherently chiral ABii diphosphonato cavitand (±)-4 bearing a single quinoxaline bridging moiety was synthesized and resolved by chiral HPLC. Its chiroptical properties were investigated and VCD experiments allowed the determination of its absolute configuration. Distinguishable diastereomeric complexes in solution with l-adrenaline were observed by 1H and 31P NMR together with a noticeable enantio-discrimination at 253 K (dr ∼2:1) in favor of the dextrorotatory cavitand (+)-4.

Dates et versions

hal-01116894 , version 1 (15-02-2015)

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Jérôme Vachon, Steven Harthong, Béatrice Dubessy, Jean-Pierre Dutasta, Nicolas Vanthuyne, et al.. The absolute configuration of an inherently chiral phosphonatocavitand and its use toward the enantioselective recognition of l-adrenaline. Tetrahedron: Asymmetry, 2010, 21 (11-12), pp.1534-1541. ⟨10.1016/j.tetasy.2010.03.028⟩. ⟨hal-01116894⟩
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