Stereoselective synthesis of all stereoisomers of vicinal and distal bis(O-2-aminoethyl)-p-tert-butylthiacalix[4]arene

Vandana Bhalla, Manoj Kumar, Tetsutaro Hattori, Sotaro Miyano

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

O,O″- and O,O′-bis(2-aminoethyl)-p-tert-butylthiacalix[4]arenes of anti conformation have been prepared by the reduction of the corresponding O,O″- and O,O′-bis(cyanomethyl) ethers. Their syn-O,O″- and O,O′-counterparts have been prepared by alternative routes via the Mitsunobu reaction of thiacalix[4]arene with N-(2-hydroxyethyl)phthalimide and the reduction of a O,O′-disiloxanediyl-bridged O″,O‴- bis(cyanomethyl) ether of 1,2-alternate conformation, respectively. These products are expected to serve as useful precursors of highly elaborated synthetic receptors, including biscalixarenes.

Original languageEnglish
Pages (from-to)5881-5887
Number of pages7
JournalTetrahedron
Volume60
Issue number28
DOIs
Publication statusPublished - 2004 Jul 5

Keywords

  • Calixarene
  • Interconversion
  • Stereoselective functionalization

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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