Recent work on several chiral NMR solvating agents will be described. Cationic and anionic cyclodextrin derivatives with high degrees of substitution are useful water-soluble reagents for anions and cations, respectively. The enantiomeric discrimination of the ionic substrates is larger than observed using neutral cyclodextrins. Prolinylmethyl derivatives of a sulfonated calix[4]resorcinarene are another family of water-soluble reagents that are useful for compounds with phenyl, pyridyl, bicyclic aromatic and indole rings. Calix[4]resorcinarene derivatives with hydroxyproline, methylproline and pipecolinic acid are more effective reagents than the proline derivative. (18-crown-6)-2,3,11,12-tetracarboxylic acid is an especially useful reagent for the analysis of primary and secondary amines. Finally, organic-soluble, diamagnetic lanthanide chelates are useful chiral NMR shift reagents for oxygen- and nitrogen-containing compounds. Complexes with aryl-substituted camphor ligands are more effective than the corresponding ligands with alkylfluoride substituent groups.

Cyclodextrins, calix[4]resorcinarenes, crown ethers and diamagnetic lanthanide complexes as chiral NMR solvating agents

244th National Meeting (2012)

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