Syntheses of chirally modified thiacalix[4]arenes with enantiomeric amines and their application to chiral stationary phases for gas chromatography

F. Narumi, N. Iki, T. Suzuki, T. Onodera, S. Miyano

研究成果: Article査読

36 被引用数 (Scopus)

抄録

New chirally modified p-tert-butylthiacalix[4] 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-butylcalix[4]arene did not indicate any enantioseparation at all for the same samples, showing that the bridging group of the calix[4]arene 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.

本文言語English
ページ(範囲)83-93
ページ数11
ジャーナルEnantiomer
5
1
出版ステータスPublished - 2000 1 1

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Organic Chemistry

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