Enantiomeric recognition of chiral 3,3-bridged-1,1 '-binaphthol dimer toward alpha-phenylethylamine and alpha-amino acid ester

The 1,1'-binaphthol-based dimers with p-phenylenebis(2-ethynyl) spacer, (+) -6 and (+)-2, were synthesized as chiral host compounds. H-1 NMR, UV-vis, a nd fluorescent titration were used to evaluate the enantiomeric recognition abilities of the chiral host dimers toward the guest amine 7 and alpha -am ino acid ester 8. The chiral BINOL-based dimers were found to have good ena ntiomeric recognition ability. The computer simulation of the host-guest co mplex molecules was carried out to describe the conformational changes of b oth naphthyl ring in the molecule of chiral host dimer after complexation w ith the guest molecule. Chirality 13:595-600, 2001. (C) 2001 Wiley-Liss, In c.