Asymmetric synthesis of ternaphthalenes via an ester-mediated nucleophilic aromatic substitution reaction

Tetsutaro Hattori, Hiroaki Iwato, Koichi Natori, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

A convenient method is presented for the asymmetric synthesis of axially chiral 1,1′:5′,1″- and 1,1′:4′,1″- ternaphthalenes via the ester-mediated nucleophilic aromatic substitution reaction. Thus, treatment of dimenthyl 1,5-dimenthoxynaphthalene-2,6- dicarboxylate 7 and its regioisomer, dimenthyl 1,4-dimenthoxynaphthalene-2,3- dicarboxylate 10, with 2-methoxynaphthalen-1-ylmagnesium bromide 12 gave enantiomerically and diastereomerically pure dimenthyl 2,2″-dimethoxy-1, 1′:5′,1″-ternaphthalene-2′,6′-dicarboxylate 3 and dimenthyl 2,2″-dimethoxy-1,1′:4′,1″-ternaphthalene- 2′,3′-dicarboxylate 4 in 70% and 63% yields, respectively, after chromatographic purification.

Original languageEnglish
Pages (from-to)881-887
Number of pages7
JournalTetrahedron Asymmetry
Volume15
Issue number5
DOIs
Publication statusPublished - 2004 Mar 8

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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