Highly Enantioselective Extraction of Phenylglycine by a Chiral Macrocyclic Receptor Based on Supramolecular Interactions

Using supramolecular interactions, a novel macrocyclic receptor is able to selectively extract zwitterionic phenylglycine from neutral aqueous solutions into chloroform with up to 91.8% ee. Modeling studies, nuclear magnetic resonance experiments, and X-ray diffraction analysis were carried out to e...

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Veröffentlicht in:	Organic letters 2020-02, Vol.22 (3), p.867-872
Hauptverfasser:	Turiel, María G, Garrido-González, José J, Simón, Luis, Sanz, Francisca, Lithgow, Anna M, Morán, Joaquín R, Fuentes de Arriba, Ángel L, Alcázar, Victoria
Format:	Artikel
Sprache:	eng
Schlagworte:	Chloroform - chemistry Crystallography, X-Ray Glycine - analogs & derivatives Glycine - chemistry Glycine - isolation & purification Macrocyclic Compounds - chemistry Models, Molecular Molecular Structure Stereoisomerism
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Beschreibung
Zusammenfassung:	Using supramolecular interactions, a novel macrocyclic receptor is able to selectively extract zwitterionic phenylglycine from neutral aqueous solutions into chloroform with up to 91.8% ee. Modeling studies, nuclear magnetic resonance experiments, and X-ray diffraction analysis were carried out to explain the high enantioselectivity observed.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/acs.orglett.9b04379