Combinatorial approach to enantiomeric discrimination: Synthesis and 19F NMR screening of a chiral ionic liquid-modified silane library

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A parallel library of chiral ionic liquid (CIL)-modified silanes as potential chiral selectors was synthesized, and their enantiomeric discrimination abilities were screened by use of 19F NMR spectroscopy. The screening method allows for rapid identification of the most enantioselective members of the library and simultaneous investigation of their chiral recognition mechanisms. The library compounds were synthesized using quaternization and anion-exchange reactions. Three major parameters (type of chiral cations, anions, and linker chain lengths) were included and investigated during the synthesis and screening. As expected, the structure of the chiral cation was found to play an important role in determining chiral recognition abilities. In addition, several types of intermolecular interactions including ion-pair, hydrogen bonding, n-n stacking, dipóle stacking, and steric interactions were found to impact chiral discrimination. © 2009 American Chemical Society.

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Journal of Combinatorial Chemistry

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