Novel chiral solvating agents derived from natural amino acid: enantiodiscrimination for chiral α-arylalkylamines

Two benzo[de]isoquinoline 1,3-dione amino acids 1 and 2 were readily prepared, and their enantiodiscriminating ability were investigated by 1H NMR spectroscopy. It was found that 1 exhibited an excellent chiral recognition ability toward chiral α-phenylethylamine and some of its derivatives, leading to clear baseline separation of the multiplet of the probe groups in two enantiomers. The stoichiometric ratio and association constants of some host–guest complexes were determined. The interactions between the hosts and guest 3 were further studied by intermolecular NOE experiment and ESI-MS.