A sulfonated calix[4]resorcinarene with l-pipecolinic acid groups as a water-soluble chiral NMR solvating agent |
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Authors: | Ngoc H Pham Thomas J Wenzel |
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Institution: | Department of Chemistry, Bates College, Lewiston, Maine 04240, USA |
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Abstract: | A water-soluble calix4]resorcinarene containing l-pipecolinic acid groups is investigated as a chiral NMR solvating agent for aromatic-containing substrates. The substrates form complexes by insertion of the aromatic ring into the cavity of calix4]resorcinarene. Compounds with phenyl, naphthyl, indole, indoline and pyridyl rings were investigated. The substrates also have ammonium or carboxylate functional groups. The effectiveness of the calix4]resorcinarene with l-pipecolinic acid groups is compared to similar reagents with proline, hydroxyproline, and α-methylproline moieties that have previously been reported. The derivative with l-pipecolinic acid usually produces better enantiomeric discrimination compared to previous calix4]resorcinarene reagents. |
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