Enantiomeric discrimination of aromatic-containing anionic substrates using cationic cyclodextrins

Cationic α-, β-, and γ-cyclodextrins were prepared by reacting the corresponding native cyclodextrin (CD) with glycidyltrimethylammonium chloride (GTAC). The reaction conditions were varied in order to alter the degree of substitution of GTAC units on the cyclodextrin. The CD-GTAC derivatives, which retain a positive charge independent of pH, were evaluated as water-soluble chiral NMR solvating agents for anionic substrates. The CD-GTAC derivatives are considerably more effective at causing enantiomeric discrimination in the 1H NMR spectra of aromatic-containing anionic substrates than the neutral native cyclodextrins. Derivatives with a degree of substitution of about 1.5 were more effective than those with lower or higher degree of substitution. Not one of the α-, β-, and γ-CD-GTAC derivatives was consistently the most effective at causing enantiomeric discrimination for all of the substrates examined herein.