Water-Soluble Calix[4]resorcinarenes with Hydroxyproline Groups as Chiral NMR Solvating Agents for Phenyl- and Pyridyl-Containing Compounds

Autor:	Thomas J. Wenzel, Courtney M. O'Farrell, Kaitlin A. Hagan
Rok vydání:	2009
Předmět:	organic chemicals Organic Chemistry Nuclear magnetic resonance spectroscopy Resorcinarene Chiral resolution chemistry.chemical_compound chemistry Benzyl alcohol Calixarene Proton NMR Organic chemistry heterocyclic compounds Physical and Theoretical Chemistry Enantiomer Cyclophane
Zdroj:	European Journal of Organic Chemistry. 2009:4825-4832
ISSN:	1099-0690 1434-193X
Popis:	A series of water-soluble sulfonated calix[4]resorcinarenes with L-proline, cis-4-hydroxy-d- and -L-proline, trans-4-hydroxy-L-proline and trans-3-hydroxy-L-proline are evaluated as chiral NMR solvating agents. The changes in chemical shifts and enantiomeric discrimination in the 1H NMR spectra of a variety of phenyl- and pyridyl-containing compounds are reported. Substrates associate by insertion of the phenyl or pyridyl ring into the cavity of the calix[4]resorcinarene. Series of compounds with methylbenzylamine and benzyl alcohol units are among those examined. For many compounds, the calix[4]resorcinarenes with the hydroxyproline groups are more effective chiral NMR solvating agents than the corresponding proline derivative. The trans-4- and trans-3-hydroxy-L-proline derivatives are especially effective as chiral NMR solvating agents. Enantiomeric discrimination in the 1H NMR spectra is often large enough to facilitate the analysis of enantiomeric purity.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Databáze:	OpenAIRE
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