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Chiral discrimination of 2-heptlyaminium salt by planar-chiral monohydroxy-functionalized pillar[5]arenes

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Abstract

This paper reports the synthesis of a planar-chiral monohydroxy-functionalized pillar[5]arene amenable to a wide variety of chemical modifications. Chiral resolution was performed using derivatization with Mosher's acid chloride (S)-(+)-α-methoxy-α-trifluoromethylphenylacetyl chloride ((S)-(+)-MTPA-Cl), and the absolute configurations of the thus obtained MTPA ester-functionalized pillar[5]arenes were determined by single-crystal X-ray diffraction. Finally, the effect of hydroxy groups on the temperature-dependent rotational movement of pillar[5]arene units was investigated by chiral HPLC and its application as a chiral receptor for alkyl aminium salts was demonstrated.

Graphical abstract: Chiral discrimination of 2-heptlyaminium salt by planar-chiral monohydroxy-functionalized pillar[5]arenes

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Publication details

The article was received on 11 Dec 2018, accepted on 18 Jan 2019 and first published on 18 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01343H
Citation: Org. Chem. Front., 2019, Advance Article

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    Chiral discrimination of 2-heptlyaminium salt by planar-chiral monohydroxy-functionalized pillar[5]arenes

    T. F. Al-Azemi, M. Vinodh, F. H. Alipour and A. A. Mohamod, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01343H

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