〔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

書誌事項

タイトル別名

• (2+2) Photocycloaddition Reaction of 5-Arylfuran-2,3-diones to Trimethylsilyloxyethylenes.
• 2+2 Photocycloaddition Reaction of 5 Ar

抄録

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.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 45 (4), 608-612, 1997

  公益社団法人 日本薬学会

キーワード

• [2+2] photocycloaddition
• dioxofuran
• cyclobutane
• stereochemistry
• trimethylsilyloxyethylene

詳細情報

• CRID: 1390282679137703808
• NII論文ID: 110003616537
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.45.608
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 4196881
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I4196881
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/45/4/45_4_608/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可