Intramolecular rearrangement of 1,3-bistriflate ester of thiacalix[4]arene to 1,2-counterpart: an efficient di-O-protection method for the stereoselective synthesis of anti-1,2-diethers

Ryuichi Serizawa, Shinya Tanaka, Naoya Morohashi, Fumitaka Narumi, Tetsutaro Hattori

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

A net anti-selective dialkylation of the proximal hydroxy groups of thiacalix[4]arene 2 is achieved for the first time via the initial protection of the two proximal hydroxy groups of compound 2 with Tf moieties by intramolecular rearrangement of easily preparable 1,3-bistriflate ester 3 to 1,2-counterpart 4, followed by anti-selective dialkylation of the remaining hydroxy groups with alkyl halides or under the Mitsunobu conditions and subsequent removal of the Tf moieties.

Original languageEnglish
Pages (from-to)6281-6285
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number36
DOIs
Publication statusPublished - 2007 Sep 3

Keywords

  • Intramolecular ester exchange
  • Thiacalix[4]arene
  • anti-Selective 1,2-dialkylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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