Proximal O,O′-capped calix[4]arenes with a disiloxane bridge as highly efficient synthetic intermediates for 1,2-dialkylation at the lower rim

Fumitaka Narumi, Naoya Morohashi, Nobuji Matsumura, Nobuhiko Iki, Hiroshi Kameyama, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

Treatment of calix[4]arenes with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane using imidazole as a base yielded O,O′-bridged calixarenes in excellent yields, which were subsequently treated with an alkyl halide/base to give O″,O‴-dialkylated products in high yields. These were, in turn, amenable to fluoride-promoted quantitative desilylation, thus providing an efficient method for the net proximal dialkylation of calix[4]arenes at the lower rim.

Original languageEnglish
Pages (from-to)621-625
Number of pages5
JournalTetrahedron Letters
Volume43
Issue number4
DOIs
Publication statusPublished - 2002 Jan 21

Keywords

  • Disyloxane
  • O,O′-bridged calix[4]arenes
  • Proximal dialkylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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