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

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8035-8038
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number45
DOIs
Publication statusPublished - 2001 Nov 5

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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