Highly stereospecific conversion of C-centrochirality of a 3,4-dihydro-2H-1,1′-binaphthalen-1-ol into axial chirality of a 3,4-dihydro-1,1′-binaphthalene

Tetsutaro Hattori, Masamitsu Date, Kenta Sakurai, Naoya Morohashi, Hiroshi Kosugi, Sotaro Miyano

研究成果: Article査読

38 被引用数 (Scopus)

抄録

C-Centrochirality of 3,4-dihydro-2′-methoxy-2-methyl-2H-1,1′-binaphthalen-1-ol (R,R)-3e, which had been prepared by diastereoselective 1,2-addition of a 2-methoxy-1-naphthylytterbium reagent to 2-methyl-1-tetralone (R)-1b, was stereospecifically converted into axial chirality of 3,4-dihydro-2′-methoxy-2-methyl-1,1′-binaphthalene (aR)-4 with up to 95% ee by dehydration with trifluoroacetic anhydride. DDQ aromatization of (aR)-4 gave 2′-methoxy-2-methyl-1,1′-binaphthalene (aR)-5 without appreciable loss of the axial integrity. The net process provides a potential access to nonracemic 1,1′-binaphthalenes.

本文言語English
ページ(範囲)8035-8038
ページ数4
ジャーナルTetrahedron Letters
42
45
DOI
出版ステータスPublished - 2001 11 5

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

フィンガープリント

「Highly stereospecific conversion of C-centrochirality of a 3,4-dihydro-2H-1,1′-binaphthalen-1-ol into axial chirality of a 3,4-dihydro-1,1′-binaphthalene」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。

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