[2+2] Photocycloaddition reaction of 5-arylfuran-2,3-diones to trimethylsilyloxyethylenes

Takehiro Sano, Nobuyuki Koseki, Toshiaki Saitoh, Yoshie Horiguchi, Jun Toda, Fumiyuki Kiuchi, Yoshisuke Tsuda

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The photocycloaddition reaction of 5-phenylfuran-2,3-dione (1a) to 2- trimethylsilyloxybutadiene proceeded in a [2s+2s] manner with high regio- and stereo-selectivities to give a 2-oxabicyclo[3.2.0]heptane-3,4-dione 2 with 7- endo-OTMS-7-exo-vinyl stereochemistry. 5-Arylfuran-2,3-diones (1a-e) on similar photocycloaddition with 1-phenyl-1-trimethylsilyloxyethylene gave the corresponding 7-aryl derivatives 3a-e with the same regio- and stereo- chemistries in good yields. This stereochemical result of O-endo selectivity is consistent with the prediction obtained from the stereo-selection rule proposed for the enone-olefin photocycloaddition reaction. The reaction provides an efficient method for the synthesis of poly-functionalized cyclobutane derivatives.

Original languageEnglish
Pages (from-to)608-612
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume45
Issue number4
DOIs
Publication statusPublished - 1997 Apr
Externally publishedYes

Keywords

  • [2+2] photocycloaddition
  • cyclobutane
  • dioxofuran
  • stereochemistry
  • trimethylsilyloxyet hylene

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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