Chemoselective ring closure of thiacalix[4]arene-1,3-bis(N-ω- hydroxyalkylamides) via the Mitsunobu reaction

Viktor Csokai, András Simon, Barbara Balázs, Gábor Tóth, István Bitter

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Chemoselective intramolecular ring closure on the phenolic OH groups of p-tert-butylthiacalix[4]arene-1,3-bis(N-ω-hydroxyalkylamides) attained under Mitsunobu conditions affords inherently chiral macrocycles capped by carboxamide bridges. Oxazoline or oxazine cyclization products derived from self-condensation of the hydroxyalkylamide moieties were not isolated. In one case the detection of enantiomers was achieved by chiral HPLC.

Original languageEnglish
Pages (from-to)2850-2856
Number of pages7
JournalTetrahedron
Volume62
Issue number12
DOIs
Publication statusPublished - Mar 20 2006

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Keywords

  • Cyclizations
  • Hydroxyalkylamides
  • Mitsunobu reaction
  • Thiacalix[4]arenes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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