Dioxopyrrolines. LV.1) Stereochemical Pathway of [2 + 2] Photocycloaddition Reaction of 4,5-Diethoxycarbony 1-1H-pyrrole-2,3-dione to Cycloalkadienes and Cycloalkenes

Takehiro Sano, Hiroshi Enomoto, Kenji Yasui, Yoshie Horiguchi, Fumiyuki Kiuchi, Yoshisuke Tsuda

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5 Citations (Scopus)

Abstract

The photocycloaddition reactions of 4,5-diethoxycarbonyl-lH-pyrrole-2,3-dione (6) to cycloalkadienes and cycloalkenes were examined. The addition of cyclopentadiene gave the hydroindole 8a (s + a product) as a major product and the cis-fused cyclobutane 7a (s + s product) as a minor one. In contrast, the addition of cyclohexadiene gave the cyclobutane 7b (s + s product) as a major product and the hydroindole 8b (s + a product) as a minor one. The photocycloaddition of cyclopentene, cyclohexene, and indene proceeded predominantly in an s + s manner to give the cis-syn-cis cyclobutanes, 16, 18, and 19, respectively. The stereochemical results were compared with those of the photocycloaddition reactions of 4-ethoxycarbonyl-5-phenyl-lH-pyrrole-2,3-dione (1) to the corresponding cyclo-olefins, revealing that the steric relationship of the addends plays an important role in determining the stereochemical pathway of the reaction.

Original languageEnglish
Pages (from-to)846-853
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume41
Issue number5
DOIs
Publication statusPublished - 1993 Jan 1

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Keywords

  • cyclobutane
  • dioxopyrroline
  • photocycloaddition
  • stereo-selection rule
  • stereochemistry
  • steric effect

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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