Chiral Recognition and Kinetic Resolution of Aromatic Amines via Supramolecular Chiral Nanocapsules in Nonpolar Solvents

Herein we report the first example
of chiral recognition and kinetic
resolution of aromatic amine guests using supramolecular nanocapsules
assembled from cyclodextrin derivatives in nonpolar media. With these
nanocapsules, an extremely high chiral recognition of 1-(1-naphthyl)­ethylamine
(1) in cyclohexane was achieved, with a binding selectivity
of up to 41 for (S)-1 over (R)-1. In addition, kinetic resolution of 1 through enantioselective N-acylation was accomplished with
an enantiomeric excess of up to 91%.