First asymmetric photosensitization in supercritical fluid. Exceptionally high pressure/density dependence of optical yield in photosensitized enantiodifferentiating isomerization of cyclooctene

Ryota Saito, Masayuki Kaneda, Takehiko Wada, Akira Katoh, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The photosensitized enantiodifferentiating isomerization of (Z)-cyclooctene (1Z) in supercritical carbon dioxide has been performed for the first time. The critical control of the enantiomeric excess (ee) of chiral product, (E)-cyclooctene (1E), and even the switching of the product's chirality were achieved through a small change of pressure particularly in the low-density region near the critical density. Quantitative evaluation of these ee changes was achieved by estimating differential activation volumes between the diastereomeric transition states of the reaction.

Original languageEnglish
Pages (from-to)860-861
Number of pages2
JournalChemistry Letters
Issue number8
DOIs
Publication statusPublished - 2002 Aug 5
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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