Dioxypyrrolines. LV. Stereochemical Pathway of [2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Cycloalkadienes and Cycloalkenes
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概要
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The photocycloaddition reactions of 4,5-diethoxycarbonyl-1H-pyrrole-2,3-dione (6) to cycloalkadienes and cycloalkenes were examined. The addition of cyclopentadiene gave the hydroindole 8a (s+a product) as a major product and the cis-fused cyclobutane 7a (s+s product) as a minor one. In contrast, the addition of cyclohexadiene gave the cyclobutane 7b (s+s product) as a major product and the hydroidole 8b (s+a product) as a minor one. The photocycloaddition of cyclopentene, cyclohexene, and indene proceeded predominantly in an s+s manner to give the cis-syn-cis cyclobutanes, 16,18,and 19,respectively. The stereochemical results were compared with those of the photocycloaddition reaction of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione (1) to the corresponding cyclo-olefins, revealing that the steric relationship of the addends plays an important role in determining the stereochemical pathway of the reaction.
- 社団法人日本薬学会の論文
- 1993-05-15
著者
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津田 喜典
金沢大学
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安井 健二
Showa College Of Pharmaceutical Sciences
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木内 文之
Faculty of Pharmaceutical Sciences, Kanazawa University
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津田 喜典
Faculty of Pharmaceutical Sciences, Kanazawa University
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榎本 浩
Showa College Of Pharmaceutical Sciences Kanazawa University
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津田 喜典
金沢大学薬学部
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津田 喜典
Faculty Of Pharmaceutical Sciences Kanazawa University
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佐野 武弘
Showa College of Pharmaceutical Sciences.
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堀口 よし江
昭和薬大
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堀口 よし江
Showa College of Pharmaceutical Sciences
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佐野 武弘
昭和薬科大学
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佐野 武弘
Showa Pharmaceutical Univ. Tokyo Jpn
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佐野 武弘
Showa College Of Pharmaceutical Sciences
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Kiuchi F
Graduate School Of Pharmaceutical Sciences Kyoto University
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堀口 よし江
Showa College Of Pharmaceutical Sciences University Of Kanazawa
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木内 文之
慶應義塾大学薬学部
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