Synthesis of an inherently chiral O,O′-bridged thiacalix[4] crowncarboxylic acid and its application to a chiral solvating agent

Fumitaka Narumi, Tetsutaro Hattori, Nobuji Matsumura, Toru Onodera, Hiroshi Katagiri, Chizuko Kabuto, Hiroshi Kameyama, Sotaro Miyano

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

Treatment of readily available O,O′-1,1,3,3-tetraisopropyldisiloxane- 1,3-diyl-bridged p-tert-butylthiacalix[4]arene (1) with tri(ethylene glycol) di-p-tosylate and subsequent desilylation gave O,O′-bridged thiacalix[4]crown 3 in an excellent yield. Mono-O-alkylation of 3 with ethyl bromoacetate, followed by optical resolution by chiral HPLC, and subsequent hydrolysis of the ester moiety gave inherently chiral O,O′-bridged thiacalix[4]crowncarboxylic acid (+)-6, which clearly discriminated enantiomeric primary amines, as well as amino esters, by 1H NMR spectroscopy.

Original languageEnglish
Pages (from-to)7827-7833
Number of pages7
JournalTetrahedron
Volume60
Issue number36
DOIs
Publication statusPublished - 2004 Aug 30

Keywords

  • Calixarene
  • Calixcrown
  • Chiral recognition
  • Inherently chiral

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of an inherently chiral O,O′-bridged thiacalix[4] crowncarboxylic acid and its application to a chiral solvating agent'. Together they form a unique fingerprint.

  • Cite this