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  • Title: An enantioselective NMR shift reagent for cationic aromatics.
    Author: Dignam CF, Richards CJ, Zopf JJ, Wacker LS, Wenzel TJ.
    Journal: Org Lett; 2005 Apr 28; 7(9):1773-6. PubMed ID: 15844903.
    Abstract:
    [structure: see text] The water-soluble tetra l-prolinylmethyl derivative of a tetrasulfonated calix[4]resorcarene is an effective chiral NMR solvating agent for compounds with bicyclic aromatic or indole rings. Complexation of bicyclic substrates with the calix[4]resorcarene is likely promoted by hydrophobic effects. The bicyclic substrates have larger association constants with the calix[4]resorcarene than similar phenyl-containing compounds. Substantial enantiomeric discrimination is observed for several resonances in the (1)H NMR spectra of these substrates.
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