Highly stereospecific conversion of planar chirality of a cyclophane into axial chirality of binaphthyls

Tetsutaro Hattori, Nobuyuki Koike, Yoshikazu Okaishi, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Reaction of oxanaphthalenophane (R)-2 with 1-naphthyl Grignard reagents 3 affords 1,1'-binaphthyls 4 of high enantiomeric purity, providing the first example of an asymmetric ring-opening of the cyclophane class of compounds. Because the stereoselectivity of the reaction coincides very well with that of the reaction of (-)-menthyl ether 1 with 3, which we reported previously, it is supposed that the steric effect of the (-)-menthoxy moiety of 1 is equivalent to that of the ansa chain of (R)-2 in these reactions.

Original languageEnglish
Pages (from-to)2057-2060
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number12
DOIs
Publication statusPublished - 1996 Mar 18

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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