Nucleophilic aromatic substitution on 1-alkoxy-2-nitronaphthalene by 1-naphthyl Grignard reagents for the synthesis of 2-nitro-1,1′-binaphthyls

Tetsutaro Hattori, Ayanobu Takeda, Osamu Yamabe, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

Treatment of 1-methoxy-2-nitronaphthalene with 1-naphthyl- and 2-methoxy-1-naphthylmagnesium bromide in diethyl ether-benzene at room temperature provides a facile entry to the corresponding 2-nitro-1,1′-binaphthyls in high yields. Induction of axial chirality into the binaphthyl bond has been achieved by using 1-menthoxy-2-nitronaphthalene as the substrate, giving 2-methoxy-2′-nitro-1,1′-binaphthyl of 78% ee. Also reported is the optical resolution of 2-amino-1,1′-binaphthyls, which can be easily prepared by reduction of the 2-nitro-1,1′-binaphthyls, by preparative LC on a cellulose-derived chiral stationary phase, or on silica gel after conversion into the diastereomeric menthyl carbamates.

Original languageEnglish
Pages (from-to)233-238
Number of pages6
JournalTetrahedron
Volume58
Issue number2
DOIs
Publication statusPublished - 2002 Jan 7

Keywords

  • Asymmetric synthesis
  • Biaryls
  • Coupling reactions
  • Nitro compounds

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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