Synthesis of an enantiomerically pure inherently chiral calix[4]arene phosphonic acid and its evaluation as an organocatalyst - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2018

Synthesis of an enantiomerically pure inherently chiral calix[4]arene phosphonic acid and its evaluation as an organocatalyst

Résumé

A facile method for the preparation of enantiomerically pure inherently chiral calix[4]arene phosphonic acid (cR,pR)-7 in four steps starting from the readily available and previously synthesized (cS)-enantiomer of calix[4]arene acetic acid 1 or its methyl ester 2 was developed. The first tests of this unique calixarene Brönsted acid with inherent chirality in organocatalysis of the aza-Diels–Alder reaction of imines with Danishefsky’s diene and epoxide ring opening by benzoic acid were performed. The calixarene phosphonic acid (cR,pR)-7 shows good catalytic activities but with low enantioselectivities in these reactions.
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Dates et versions

hal-02129142 , version 1 (14-05-2019)

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Andrii Karpus, Oleksandr Yesypenko, Vyacheslav Boiko, Jean-Claude Daran, Zoia Voitenko, et al.. Synthesis of an enantiomerically pure inherently chiral calix[4]arene phosphonic acid and its evaluation as an organocatalyst. Journal of Organic Chemistry, 2018, 83 (3), pp.1146-1153. ⟨10.1021/acs.joc.7b02312⟩. ⟨hal-02129142⟩
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