New chirally modified p-tert-butylthiacalix arenes were synthesized via conformation- and/or regioselective etherification with ethyl bromoacetate followed by hydrolysis of the ester moiety and then subsequent amidation with (S)-1-phenyl-ethylamine or (S)-1-(1-naphthyl)ethylamine. These chiral selectors were coated with OV-17 on capillary columns to examine their ability as chiral stationary phases (CSPs) for discrimination of enantiomeric amino acid, amine and alcohol derivatives. It was found that CSP-(S)-4 prepared from cone-shaped tetra-(S)-1-phenylethylamide (S)-4 showed good to fair separations for all the samples examined. On the contrary, the corresponding CSP-(S)-14 prepared from the cone-shaped tetraamide (S)-14 of the parent p-tert-butylcalixarene did not indicate any enantioseparation at all for the same samples, showing that the bridging group of the calixarene ring is critical for the advent of enantioselectivity. The effect of the types and the numbers of the chiral amide groups in the chiral selectors on enantioselectivity was also discussed.
|出版ステータス||Published - 2000 1 1|
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Organic Chemistry