Dioxopyrrolines. LIII.Stereochemical Pathway of [2+2] Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Cyclic Enol Trimethylsilyl Ethers

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概要

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• The photocycloaddition reaction of the dioxopyrroline 1 to cyclic trimethylsilyloxy olefins was examined. The addition of 3-trimethylsilyloxy-1H-indene and 4-trimethylsilyloxy-1,2-dihydronaphthalene occurred in a regio- and stereoselective manner to give the cis-anti-cis cyclobutanes 3 and 4,respectively. The stereochemical result supported the stereo-selection rule which states that the photocycloaddition of a very polar dioxopyrroline-olefin pair proceeds in an s+s manner via f favored O-endo-π-complex transition. On the other hand, the addition of 1-trimethylsilyloxy-cyclopentene and 1-trimethylsilyloxycyclohexene occurred less stereoselectively, proceeding predominantly in an s+a manner to give the adducts 5a, b, 6a, b, 7a, b, and 12. The results are consistent with the prediction of the stereo-selection rule obtained by assuming that these dioxopyrroline-olefin pairs are polar. The latter cases demonstrate that an incresed steric hindrance around the olefin moiety affects the polarity of enone-olefin pair in the transition state.

• 社団法人日本薬学会の論文
• 1993-01-15

著者

• 津田 喜典

  金沢大学

• 木内 文之

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 津田 喜典

  金沢大学薬学部

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 佐野 武弘

  Showa College of Pharmaceutical Sciences.

• 堀口 よし江

  昭和薬大

• 堀口 よし江

  Showa College of Pharmaceutical Sciences

• 廣瀬 美由紀

  Showa College of Pharmaceutical Sciences, University of Kanazawa

• 佐野 武弘

  昭和薬科大学

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• 佐野 武弘

  Showa College Of Pharmaceutical Sciences

• 広瀬 美由紀

  Showa College Of Pharmaceutical Sciences University Of Kanazawa

• Kiuchi F

  Graduate School Of Pharmaceutical Sciences Kyoto University

• 堀口 よし江

  Showa College Of Pharmaceutical Sciences University Of Kanazawa

• 木内 文之

  慶應義塾大学薬学部

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