1997年4月
[2+2] photocycloaddition reaction of 5-arylfuran-2,3-diones to trimethylsilyloxyethylenes
CHEMICAL & PHARMACEUTICAL BULLETIN
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- 巻
- 45
- 号
- 4
- 開始ページ
- 608
- 終了ページ
- 612
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1248/cpb.45.608
- 出版者・発行元
- PHARMACEUTICAL SOC JAPAN
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.
- リンク情報
- ID情報
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- DOI : 10.1248/cpb.45.608
- ISSN : 0009-2363
- CiNii Articles ID : 110003616537
- Web of Science ID : WOS:A1997WU88600006