Diastereoselective [2 + 2] Photocycloaddition of Stilbene to Chiral Fumarate. Direct versus Charge-Transfer Excitation

Hideaki Saito, Tadashi Mori, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)

Abstract

The selective excitation of the charge-transfer (CT) complex and the direct excitation of the substrate gave distinctly different product ratios and diastereomeric excesses (de's), as well as their temperature dependencies, in [2 + 2] photocycloaddition of (E)-stilbene to bis((R)-1-methylpropyl) fumarate, clearly demonstrating that the excited CT complex and the conventional exciplex differ in structure and reactivity. This conclusion is supported by the contrasting fluorescence behavior exhibited by the relevant excited species, particularly at low temperatures.

Original languageEnglish
Pages (from-to)1900-1906
Number of pages7
JournalJournal of the American Chemical Society
Volume126
Issue number6
DOIs
Publication statusPublished - 2004 Feb 18
Externally publishedYes

ASJC Scopus subject areas

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

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