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

研究成果: Article査読

23 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)233-238
ページ数6
ジャーナルTetrahedron
58
2
DOI
出版ステータスPublished - 2002 1 7

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

フィンガープリント

「Nucleophilic aromatic substitution on 1-alkoxy-2-nitronaphthalene by 1-naphthyl Grignard reagents for the synthesis of 2-nitro-1,1′-binaphthyls」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル