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The Development of an Environmentally Friendly and Mild Synthesis Method for Furans

Research Project

Project/Area Number 24550055
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionHiroshima University

Principal Investigator

KOJIMA Satoshi  広島大学, 理学(系)研究科(研究院), 准教授 (70215242)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsフラン / 弱酸 / 第4級炭素 / ジカルボニル化合物 / 環境調和 / 8-フェニルメンチル基 / ジアステレオ選択性 / フラン合成 / 8-フェニルメンチル基 / シスアルケン / 不斉第4級炭素 / 穏和 / 第4級不斉炭素 / 8-フェニルメンチル / βーケトエステル / フッ素化アルコール / 室温
Outline of Final Research Achievements

For reactions using 2-benzyloxycarbonylcyclopentanone as the donor and cis-4-oxo-2-pentenal as the acceptor, the Michael addition reaction had been found to occur in the presence of base. However, in the absence of base, furans bearing a quaternary carbon substituent in the 2-position were found to form under the mild temperature condition of room temperature. The furan forming reaction was found to be accelerated in the presence of weak acids such as hexafluoroisopropyl alcohol and benzoic acid. Asymmetric reactions using the 8-phenylmenthyl group as a chiral auxiliary was found to proceed with diastereoselectivity up to 96% de.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (25 results)

All 2015 2014 2013 2012

All Journal Article (14 results) (of which Peer Reviewed: 14 results,  Open Access: 1 results) Presentation (11 results)

  • [Journal Article] Formation of isomerized E,Z-configured 1,3-dienes in construction of macrocyclic trienes by diene-ene RCM2015

    • Author(s)
      R. Takagi, K. Tanaka, K. Yamamoto, Y. Hiraga, S. Kojima, M. Abe
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 88 Issue: 1 Pages: 146-148

    • DOI

      10.1246/bcsj.20140250

    • NAID

      130004690771

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] A Highly Efficient Cooperative Effect in an Acylation Catalyst Bearing Weak Lewis Base and Lewis Acid Sites2014

    • Author(s)
      S. Kojima, N. Banden, Y. Yamamoto
    • Journal Title

      Chem. Lett.

      Volume: 43 Issue: 8 Pages: 1266-1268

    • DOI

      10.1246/cl.140343

    • NAID

      130004677570

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Diastereoselective Synthesis of Chiral Furans with a Quaternary Carbon Substituent at the 2-Position Using 8-Phenylmenthol as the Chiral Auxiliary2014

    • Author(s)
      A. Katori, Y. Sashihara, A. Iwamoto, S. Kojima, Y. Yamamoto
    • Journal Title

      Chem. Lett.

      Volume: 印刷中 Issue: 6 Pages: 766-768

    • DOI

      10.1246/cl.140052

    • NAID

      130004868161

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Application of a New Dipyrido-Annulated N-Heterocyclic Carbene with Phosphorus-Substituents2014

    • Author(s)
      S.-i. Fuku-en, J. Yamamoto, S. Kojima, Y. Yamamoto,
    • Journal Title

      Chem. Lett.

      Volume: 43(4) Issue: 4 Pages: 468-470

    • DOI

      10.1246/cl.131074

    • NAID

      130004868053

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A novel non-metathetic behavior of Grubbs catalyst: Ruthenium-mediated intramolecular [3+2] cycloaddition of bis-1,3-dienes2013

    • Author(s)
      Ryukichi Takagi, Koumei Yamamoto, Yoshikazu Hiraga, Satoshi Kojima, Manabu Abe
    • Journal Title

      Journal of Organometallic Chemistry

      Volume: 723 Pages: 171-175

    • DOI

      10.1016/j.jorganchem.2012.09.004

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Impact of Diradical Character on Two-Photon Absorption : Bis(acridine) Dimers Synthesized from an Allenic Precursor2013

    • Author(s)
      Kenji Kamada, Shin-ichi Fuku-en. Shu Minamide, Koji Ohta, Ryohei Kishi, Masayoshi Nakano, Hiroyuki Matsuzaki, Hiroshi Okamoto, Hiroyuki Higashikawa, Katsuya Inoue, Satoshi Kojima, Yohsuke Yamamoto
    • Journal Title

      Journal of the American Chemical Society

      Volume: 135(1) Issue: 1 Pages: 232-241

    • DOI

      10.1021/ja308396a

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Novel 7-6-7 Ring Based PCP Pincer Rhodium Complexes2013

    • Author(s)
      Y. Shi , S. Kojima, Y. Yamamoto
    • Journal Title

      Phosphorus, Sulfur, and Silicon and the Related Elements

      Volume: 188(1-3) Issue: 1-3 Pages: 116-120

    • DOI

      10.1080/10426507.2012.743137

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Highly active catalysts for the transfer dehydrogenation of alkanes: synthesis and application of novel 7-6-7 ring-based pincer iridium complexes2013

    • Author(s)
      Shi, Yuan; Suguri, Takuya; Dohi, Chisato; Yamada, Hirotsuna; Kojima, Satoshi; Yamamoto, Yohsuke
    • Journal Title

      Chemistry - A European Journal

      Volume: 19 Issue: 32 Pages: 10672-10689

    • DOI

      10.1002/chem.201203108

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the most anti-aromatic 16π porphyrin : an octaethylporphyrin zinc(II) complex with no meso-substituents2013

    • Author(s)
      Shogo Hiramatsu, Shun Sugawara, Satoshi Kojima, Yohsuke Yamamoto
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 17 Issue: 12 Pages: 1183-1187

    • DOI

      10.1142/s1088424613501009

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of New Dipyrido-Annulated N-Heterocyclic Carbenes with Ortho-Substituents2013

    • Author(s)
      Shin-ichi Fuku-en, Junki Yamamoto, Mao Minoura, Satoshi Kojima, and Yohsuke Yamamoto
    • Journal Title

      Inorganic Chemistry

      Volume: 52(20) Issue: 20 Pages: 11700-11702

    • DOI

      10.1021/ic402301u

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Characterization and Spectroscopic Analysis of Antiaromatic Benzofused Metalloporphyrin Species2012

    • Author(s)
      S. Sugawara, Y. Hirata, S. Kojima, Y, Yamamoto, E. Miyazaki, K. Takimiya, S. Matsukawa, D. Hashizume, J. Mack, N. Kobayashi, Z. Fu, K. M. Kadish, Y. M. Sung, K. S. Kim, D. Kim
    • Journal Title

      Chemistry-A European Journal

      Volume: 18(12) Issue: 12 Pages: 3566-3581

    • DOI

      10.1002/chem.201101846

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of new cyclic aromatic carbene ligands bearing remote amino groups and their palladium(II) complexes2012

    • Author(s)
      Shun Sugawara, Satoshi Kojima, Yohsuke Yamamoto
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 78 Pages: 9735-9737

    • DOI

      10.1039/c2cc33510g

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Anti-apicophilic Arsoranes and Related compounds.2012

    • Author(s)
      X.-D. Jiang, S. Matsukawa, S. Kojima, and Y. Yamamoto.
    • Journal Title

      Inorganic Chemistry

      Volume: 51 Issue: 20 Pages: 10996-11006

    • DOI

      10.1021/ic3014893

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Mild Synthesis of Furans with a Quaternary Carbon Substituent at the 2-Position.2012

    • Author(s)
      A. Iwamoto, A. Katori, Y. Sashihara, and S. Kojima
    • Journal Title

      Chemistry Letters

      Volume: 41 Issue: 12 Pages: 1586-1587

    • DOI

      10.1246/cl.2012.1586

    • NAID

      130004426457

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 弱いLewis酸とLewis塩基によるカルボニル活性化の検討2014

    • Author(s)
      晩田成美, 小島聡志,山本陽介
    • Organizer
      第41回有機典型元素化学討論会
    • Place of Presentation
      山口県宇部市
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] The Development and Application of New Nucleophilic Organic Catalysts2014

    • Author(s)
      A. Tamaki, S. Kojima, Y. Yamamoto
    • Organizer
      the twenty-fourth French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      Lyon, France
    • Year and Date
      2014-09-14 – 2014-09-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] Efficient Acylation Using Catalysts Bearing Weak Lewis Base and Lewis Acid Sites2014

    • Author(s)
      N. Banden, S. Kojima, Y. Yamamoto
    • Organizer
      the twenty-fourth French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      Lyon, France
    • Year and Date
      2014-09-14 – 2014-09-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of New Dipyrido-Annulated NHCs with Ortho Substituents2014

    • Author(s)
      J. Yamamoto, S.-i. Fuku-en, M. Minoura, S. Kojima, and Y. Yamamoto
    • Organizer
      ICOMC 2014 Post-Symposium in Osaka
    • Place of Presentation
      大阪
    • Year and Date
      2014-07-19
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of New Dipyrido-Annulated NHCs with Ortho Substituents2014

    • Author(s)
      J. Yamamoto, S.-i. Fuku-en, M. Minoura, S. Kojima, and Y. Yamamoto
    • Organizer
      XXVI The International Conference on Organometallic Chemistry
    • Place of Presentation
      札幌
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] 塩基と酸の協働作用によるアシル化反応の検討2013

    • Author(s)
      晩田成美・小島聡志・山本陽介
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] アシル化反応に置けるテトラキス(2-ピリジル)スタナンによる恊働効果2013

    • Author(s)
      晩田成美
    • Organizer
      第29回若手化学者のための化学道場
    • Place of Presentation
      広島
    • Related Report
      2013 Research-status Report
  • [Presentation] Diastereoselective furan synthesis and elucidation of stereochemistry2013

    • Author(s)
      KATORI, Aki; SASHIHARA, Yoshiaki; KOJIMA, Satoshi; YAMAMOTO, Yohsuke
    • Organizer
      National Organic Chemistry Symposium 2013
    • Place of Presentation
      シアトル,米国
    • Related Report
      2013 Research-status Report
  • [Presentation] ジアステレオ選択的フラン合成反応の条件検討と立体化学の解明2012

    • Author(s)
      香取亜希・指原慶彰・小島聡志・山本陽介
    • Organizer
      第2回CSJ化学フェスタ2012
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] Hexacoordinate Phosphates Bearing Either Martin Ligands or Extended Martin Ligands2012

    • Author(s)
      Yuya Toya, Satoshi Kojima, and Yohsuke Yamamoto
    • Organizer
      The 19th International Congress on Phosphorus Chemistry
    • Place of Presentation
      ロッテルダム,オランダ
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis and Characterization of Phosphoranes Bearing a Hydrazine or a Diazene Substituent2012

    • Author(s)
      Satoshi Kojima, Yuya Toya, Xin-Dong Jiang, and Yohsuke Yamamoto
    • Organizer
      The 19th International Congress on Phosphorus Chemistry
    • Place of Presentation
      ロッテルダム,オランダ
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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