[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
Publication statusPublished - 1997 Apr
Externally publishedYes

Fingerprint

Cyclobutanes
Stereochemistry
Alkenes
Derivatives
Stereoselectivity
3-oxabicyclo(3.2.0)heptane

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Sano, T., Koseki, N., Saitoh, T., Horiguchi, Y., Toda, J., Kiuchi, F., & Tsuda, Y. (1997). [2+2] Photocycloaddition reaction of 5-arylfuran-2,3-diones to trimethylsilyloxyethylenes. Chemical and Pharmaceutical Bulletin, 45(4), 608-612.

[2+2] Photocycloaddition reaction of 5-arylfuran-2,3-diones to trimethylsilyloxyethylenes. / Sano, Takehiro; Koseki, Nobuyuki; Saitoh, Toshiaki; Horiguchi, Yoshie; Toda, Jun; Kiuchi, Fumiyuki; Tsuda, Yoshisuke.

In: Chemical and Pharmaceutical Bulletin, Vol. 45, No. 4, 04.1997, p. 608-612.

Research output: Contribution to journalArticle

Sano, T, Koseki, N, Saitoh, T, Horiguchi, Y, Toda, J, Kiuchi, F & Tsuda, Y 1997, '[2+2] Photocycloaddition reaction of 5-arylfuran-2,3-diones to trimethylsilyloxyethylenes', Chemical and Pharmaceutical Bulletin, vol. 45, no. 4, pp. 608-612.
Sano, Takehiro ; Koseki, Nobuyuki ; Saitoh, Toshiaki ; Horiguchi, Yoshie ; Toda, Jun ; Kiuchi, Fumiyuki ; Tsuda, Yoshisuke. / [2+2] Photocycloaddition reaction of 5-arylfuran-2,3-diones to trimethylsilyloxyethylenes. In: Chemical and Pharmaceutical Bulletin. 1997 ; Vol. 45, No. 4. pp. 608-612.
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