New sulfonate-based chiral salts were prepared from amino alcohols and sodium hydroxymethanesulfonate, vinyl sulfonate, or sultone. The synthesis started with different amino acids from the chiral pool and gave the desired products in just four steps. After cation metathesis, the salts were explored as chiral solvating agents (CSAs) in NMR studies. The new chiral ionic liquids (CILs) were successfully able to interact with different chiral guest molecules and formed diastereomeric aggregates. In some cases, baseline separation was observed. The influence of the structural differences in the CIL as well as the structural requirements of the guest molecule is discussed.
Keywords: DFT calculation; NMR spectroscopy; amino acids; chiral anions; chiral solvating agents; sulfonic acids.
© 2023 The Authors. Chirality published by Wiley Periodicals LLC.