Dioxopyrrolines. XXXVII. Stereochemical Pathways of Dioxopyrroline-Olefin Pbotocycloaddition. Stereochemical Selection Rule for the Photocycloaddition of Enone-Olefin Pairs(Organic,Chemical)

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• The photocycloaddition of 4-ethoxycarbonyl-5-phenyl-2H-pyrrole-2,3-dione 1 to (Z)- and (E)-d-styrenes proceeded in a stereoselective manner to give the compounds in whieh the styrene component added to 1 antarafacially as the major products. Including these results, the observed exo- or endo-stereoselectivity in the photocycloaddition of 1 to various acyclic olefins is well explaincd by assuming plural transition states, stepwise C-C bond formation, and a stereo-selection rule which may be stated as follows: 1) the first C-C bond formation always occurs suprafacially; 2) the second C-C bond formation in a polar enone-olefin pair (an enone and an olefin with a weak electron donating substituent) accurs antara-selectively from the favored π-complex, while it occurs supra-selectively from the less favored transition state; and 3) in a very polar enone-olefin pair (an enone and an olefin with a strong electron donating group), the second C-C bond formation occurs supra-selectively from the favored π-complex and antara-selectively from the less-favored transition state. Many other stereochemicai results hitherio reported can be rationalized in terms of this stereo-selection rule.

• 公益社団法人日本薬学会の論文
• 1987-01-25

著者

• 津田 喜典

  Faculty 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

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• 佐野 武弘

  Showa College Of Pharmaceutical Sciences

• 堀口 よし江

  Showa College Of Pharmaceutical Sciences University Of Kanazawa

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