Dioxopyrrolines. XLVI. : [2+2] Photocycloaddition of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Six-Membered Cycloolefins : Effect of Ring Size on Stereochemical Pathways

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概要

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• Photocycloaddition reaction of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione (1) with cyclohexadiene and dihydropyran gave the cis-fused cyclobutane 5b and the trans-fused cyclobutane 6b as major adducts, respectively. The structures including stereochemistry were established by X-ray crystallographic analysis.The results for these systems markedly contrast with those for the photocycloaddition of 1 to five-membered cycloolefins, cyclopentadiene and dihydrofuran, which yield the adducts with skeletal rearrangements. The difference of product depending on the ring size can be related to the difference in the stereochemical pathways. The distance between donor and aceeptor is suggested to be an important factor determining the polarity of the donor-acceptor pair and, therefore, the stereochemistry of the photocycloaddition.

• 公益社団法人日本薬学会の論文
• 1990-02-25

著者

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 小倉 治夫

  School of Pharmaceutical Sciences, Kitasato University

• 高柳 弘明

  School of Pharmaceutical Sciences, Kitasato University

• 小倉 治夫

  北里大学

• 小倉 治夫

  School Of Pharmaceutical Sciences Kitasato University

• 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

• 高柳 弘明

  北里大学薬学部薬化学教室

• 高柳 弘明

  School Of Pharmaceutical Sciences Kitasato University

• 津田 喜典

  金沢大薬

• 堀口 よし江

  Showa College of Pharmaceutical Sciences

• 今福 一江

  Showa College of Pharmaceutical Sciences

• 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

• 堀口 よし江

  Showa College Of Pharmaceutical Sciences University Of Kanazawa

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