Synthesis and properties of S,R-alternating octinaphthalenes

Kazuto Takaishi, Daisuke Sue, Shunsuke Kuwahara, Nobuyuki Harada, Takeo Kawabata, Kazunori Tsubaki

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

(S,R,S,R,S,R,S)- and (S,R,S,S,S,R,S)-octinaphthalenes were synthesized by oxidative coupling of (S,R,S)-quaternaphthalene, and differences due to axis chirality of (S,R,S,R,S,R,S)-, (S,R,S,S,S,R,S)-, (S,S,S,R,S,S,S)-, and (S,S,S,S,S,S,S)-octinaphthalenes were compared using the Rf values on TLC, specific optical rotations, 1H NMR chemical shifts of the hydroxy groups, and CD spectra. A clear CD additivity was found in the Δε values of the 1La transition around 290 nm, which are proportional to the difference between the numbers of S and R binaphthalene units.

Original languageEnglish
Pages (from-to)6135-6140
Number of pages6
JournalTetrahedron
Volume65
Issue number31
DOIs
Publication statusPublished - Aug 1 2009
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Takaishi, K., Sue, D., Kuwahara, S., Harada, N., Kawabata, T., & Tsubaki, K. (2009). Synthesis and properties of S,R-alternating octinaphthalenes. Tetrahedron, 65(31), 6135-6140. https://doi.org/10.1016/j.tet.2009.05.040