Entrainer effect on photochirogenesis in near-and supercritical carbon dioxide: Dramatic enhancement of enantioselectivity

Yasuhiro Nishiyama, Takehiko Wada, Sadayuki Asaoka, Tadashi Mori, Taylor A. McCarty, Nadine D. Kraut, Frank V. Bright, Yoshihisa Inoue

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Diethyl ether added as an entrainer (cosolvent) to near- and supercritical CO2 significantly enhanced the enantioselectivity of photocyclization of 5,5-diphenyl-4-penten-1-ol sensitized by saccharide naphthalenedicarboxylate to give a cyclization product in enantiomeric excesses much larger than those obtained in conventional organic solvents, revealing the unique features of nc- and sc-CO2 as well as the critical role of entrainer clustering to the intervening diastereomeric exciplex pair.

Original languageEnglish
Pages (from-to)7526-7527
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number24
DOIs
Publication statusPublished - 2008 Jun 18
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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