Dioxopyrroline. LIV. Steretchemical Pathway of[2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Acyclic Olefins

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概要

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• The photocycloaddition reaction of 4,5-diethoxycarbonyl-1H-pyrrole-2,3-dione 4 to acyclic olefins proceeded in a regioselective manner to give two head to tail adducts, the exo- (5) and endo-isomers (6). The stereochemistry of the 7-substituents of the adducts changed depeding on the electronic properties of olefins. Olefins with O-substituents(ethoxyethylene, acetoxyethylene) stereoselectively gave the endo-adducs (6d, e). Olefins with phenyl and ethyl substituents, styrene and 1-butene, gave a mexture of the exo- (5a, b) and endo-adducts (6a, b) with exo-preference.Butadiene gave the exo- (5b) and endo-adduct (6b) with slight excess of the latter. These stereochemical results are in good accordance with the predictions obtained by the sterep-selection rule of enone-olefin photocycloaddition.

• 社団法人日本薬学会の論文
• 1993-03-15

著者

• 津田 喜典

  金沢大学

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 榎本 浩

  Showa College Of Pharmaceutical Sciences Kanazawa 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

• 津田 喜典

  金沢大薬

• 堀口 よし江

  Showa College of Pharmaceutical Sciences

• 紅林 靖子

  Showa College of Pharmaceutical Sciences, Kanazawa University

• 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

• 紅林 靖子

  Showa College Of Pharmaceutical Sciences Kanazawa University

• 堀口 よし江

  Showa College Of Pharmaceutical Sciences University Of Kanazawa

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