Supramolecular photochirogenesis. 3. Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by 6-0-mono(o-methoxybenzoyl)-β-cyclodextrin

Yunyan Gao, Maki Inoue, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Supramolecular enantiodifferentiating photoisomerization of (Z)-cyclooctene (1Z) to chiral (E)-isomer (1E) through inclusion and sensitization by 6-O-mono(o-methoxybenzoyl)-β-cyclodextrin (2) was investigated in water and in aqueous methanol solutions at various temperatures. A dramatic inversion of the product chirality was observed to occur by simply changing the solvent from water to methanol. Thus, the supramolecular photosensitization in aqueous solution gave (R)-(-)-1E in 15% enantiomeric excess (ee), whereas in methanol the antipodal (S)-(+)-1E was obtained in 5% ee. The temperature and solvent dependencies of the product ee are discussed.

Original languageEnglish
Pages (from-to)111-114
Number of pages4
JournalJournal of Inclusion Phenomena
Volume50
Issue number1-2
DOIs
Publication statusPublished - 2004 Oct

Keywords

  • Asymmetric synthesis
  • Cyclodextrin
  • Cyclooctene
  • Photochirogenesis
  • Photoisomerization

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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