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2005 Fiscal Year Final Research Report Summary

Asymmetric Photoreactions Using Microscopic Spaces

Research Project

Project/Area Number 15350026
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOsaka Prefecture University

Principal Investigator

MIZUNO Kazuhiko  Osaka Prefecture University, Graduate School of Engineering, Professor, 工学研究科, 教授 (10109879)

Co-Investigator(Kenkyū-buntansha) MAEDA Hajime  Osaka Prefecture University, Graduate School of Engineering, Research Associate, 工学研究科, 助手 (40295720)
Project Period (FY) 2003 – 2005
KeywordsAsymmetric photoreaction / Diastereoselectivity / Enantioselectivity / Minute space / Microreactor / Flow system / Zeolite / Hydrogen bonding
Research Abstract

Photochemical reactions using microscopic spaces were investigated to develop highly efficient and stereoselective photoreactions. The following results were obtained.
(1)Control of intramolecular photocycloaddition of 1-cyanonaphthalene derivatives was studied in microreactors. By using the microreactors and flow system, both the efficiency and regioselectivity in the intramolecular photocycloaddition increased compared with those under batch conditions. An increase of efficiency can be attributed to thorough absorption of light in the thin ditch. Highly regioselective photoreaction was explained by flowing out of the initial product.
(2)Asymmetric induction in photochemical reactions was investigated using chirally modified zeolites. Enantiomeric excesses (ee) was dependent on the structures of chiral materials adsorbed in zeolite cavity, SiO_2 / Al_2O_3 ratio, alkali metal cations in zeolites, molar ratio of substrates and chiral sources, and conversion of the reaction.
(3)Stereocontro … More l in Photoalkylation and photoreduction of electron-deficient alkenes by allylic silanes was examined. Diastereomeric excesses (de) of products changed depending on the structures and stoichiometry of the added carboxylic acids. High diastereoselectivity can be attained when equimolar carboxylic acids bearing bulky substituents or hydroxy group at β-position were added.
(4)Oxidative photodimerization of conjugated dienes proceeded in the presence of catalytic amount of 9-cyanophenanthrene to give nucleophile-incorporated photodimers of dienes in high yields. When chiral compounds were used as dienes or proton donors, enantioselective formation of 9-cyano-9,10-dihydrophenanthrene was observed.
(5)Hydrogen bonding was effective for stereoselective photoreactions. Highly diastereoselective photocycloadditions of vinyl ethers and furan derivatives to electron-deficient naphthalene derivatives occurred to give (2+2) and caged cycloadducts via intermolecular hydrogen bonding in the ground states. Less

  • Research Products

    (14 results)

All 2006 2005 2004

All Journal Article (12 results) Book (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Alkynylpyrenes as Improved Pyrene-Based Biomolecular Probes Having the Advantages of High Fluorescence Quantum Yields and Long Absorption/Emission Wavelengths2006

    • Author(s)
      H.Maeda, T.Maeda, K.Mizuno, K.Fujimoto, H.Shimizu, M.Inouye
    • Journal Title

      Chem.Eur.J. 12・3

      Pages: 824-831

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Formation of Caged Compounds in the Photocycloaddition of Furan to 2-, 2,3-, and 2,6-Substituted Naphthalenes via Dipole-Dipole Interaction2006

    • Author(s)
      K.Mizuno, Y.Tachibana, G.Konishi, K.Chiyonobu, H.Maeda
    • Journal Title

      J.Chin.Chem.Soc. 53・1

      Pages: 75-78

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Catalytic Ability of 9-Cyanophenanthrene in Oxidative Photodimerization of 2,5-Dimethyl-2,4-hexadiene2006

    • Author(s)
      M.Ohashi, H.Maeda, K.Mizuno
    • Journal Title

      Chem.Lett. 35・5

      Pages: 482-483

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Alkynylpyrenes as Improved Pyrene-Based Biomolecular Probes Having the Advantages of High Fluorescence Quantum Yields and Long Absorption/Emission Wavelengths2006

    • Author(s)
      H.Maeda, T.Maeda, K.Mizuno, K.Fujimoto, H.Shimizu, M.Inouye
    • Journal Title

      Chem.Eur.J. 12(3)

      Pages: 824-831

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Formation of Caged Compounds in the Photocycloaddition of Furan to 2-, 2,3-, and 2,6-Substituted Naphthalenes via Dipole-Dipole Interaction2006

    • Author(s)
      K.Mizuno, Y.Tachibana, G.Konishi, K.Chiyonobu, H.Maeda
    • Journal Title

      J.Chin.Chem.Soc. 53(1)

      Pages: 75-78

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Catalytic Ability of 9-Cyanophenanthrene in Oxidative Photodimerization of 2,5-Dimethyl-2,4-hexadiene2006

    • Author(s)
      M.Ohashi, H.Maeda, K.Mizuno
    • Journal Title

      Chem.Lett. 35(5)

      Pages: 482-483

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Photoalkylation of 2,3-Dicyanonaphthalene by Methoxy-Substituted 1,2-Diarylcyclopropanes2005

    • Author(s)
      H.Maeda, N.Matsukawa, K.Shirai, K.Mizuno
    • Journal Title

      Tetrahedron Lett. 46・17

      Pages: 3057-3060

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Photoalkylation of 2,3-Dicyanonaphthalene by Methoxy-Substituted 1,2-Diarylcyclopropanes2005

    • Author(s)
      H.Maeda, N.Matsukawa, K.Shirai, K.Mizuno
    • Journal Title

      Tetrahedron Lett. 46(17)

      Pages: 3057-3060

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Diastereoselectivity in (2π+2π) Photocycloaddition of Cholesteryl Cinnamate to Methyl 9-Phenanthrenecarboxylate : Control of the Stereoselectivity in Liquid Crystalline Phase2004

    • Author(s)
      H.Maeda, A.Horiuchi, N.Koshio, K.Mizuno
    • Journal Title

      Chem.Lett. 33・8

      Pages: 966-967

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Diastereoselective Protonation on Radical Anions of Electron-Deficient Alkenes via Photoinduced Electron Transfer2004

    • Author(s)
      T.Hayamizu, H.Maeda, K.Mizuno
    • Journal Title

      J.Org.Chem. 69・15

      Pages: 4997-5004

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Diastereoselectivity in (2π+2π) Photocycloaddition of Cholesteryl Cinnamate to Methyl 9-Phenanthrenecarboxylate : Control of the. Stereoselectivity in Liquid Crystalline Phase2004

    • Author(s)
      H.Maeda, A.Horiuchi, N.Koshio, K.Mizuno
    • Journal Title

      Chem.Lett. 33(8)

      Pages: 966-967

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Diastereoselective Protonation on Radical Anions of Electron-Deficient Alkenes via Photoinduced Electron Transfer2004

    • Author(s)
      T.Hayamizu, H.Maeda, K.Mizuno
    • Journal Title

      J.Org.Chem. 69(15)

      Pages: 4997-5004

    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] 第5版 実験化学講座 13 有機化合物の合成I-炭化水素・ハロゲン化合物-2004

    • Author(s)
      水野一彦, 他
    • Total Pages
      485
    • Publisher
      丸善株式会社
    • Description
      「研究成果報告書概要(和文)」より
  • [Patent(Industrial Property Rights)] 光反応の特性を利用する高選択的新規ベンゾ四環系化合物の一段階合成法の開発2005

    • Inventor(s)
      水野 一彦, 前多 肇 迎 弘文
    • Industrial Property Rights Holder
      大阪府立大学
    • Industrial Property Number
      特許,特願2005-259090
    • Filing Date
      2005-09-07
    • Description
      「研究成果報告書概要(和文)」より

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Published: 2007-12-13  

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