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

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)83-93
Number of pages11
JournalEnantiomer
Volume5
Issue number1
Publication statusPublished - 2000 Jan 1

Keywords

  • Calixarene
  • Chiral stationary phases
  • Chirally modified thiacalixarene
  • Gas chromatography
  • Optically pure amines
  • Thiacalixarene

ASJC Scopus subject areas

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

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