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2009 Fiscal Year Final Research Report

Activation of Carbon-Carbon Bonds by Transition Metals

Research Project

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Project/Area Number 19205013
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

MURAKAMI Masahiro  Kyoto University, 大学院・工学研究科, 教授 (20174279)

Co-Investigator(Kenkyū-buntansha) MATSUDA Takanori  東京理科大学, 理学部, 講師 (80359778)
Project Period (FY) 2007 – 2009
Keywords炭素-炭素結合切断 / 炭素-炭素結合形成 / 遷移金属触媒 / 白金 / 多環芳香族炭化水素 / アズレン / 不活性結合活性化 / 環化異性化反応
Research Abstract

New carbon-carbon bond cleaving reactions catalyzed by transition metals were developed. Various carbon skeletons were constructed by utilization of these reactions. In particular, enantioselective cleavage of a carbon-carbon bond led to the formation of quaternary chiral carbon centers. For example, six-membered benzolactones having a chiral quaternary center at the benzylic position were synthesized with high enantioselectivity. Indane skeletones having chiral quaternary centers at both benzylic positions were constructed in a stereoselective manner from cyclobutanols with an aryl substituent at the 3-position. A new method to synthesize azulene derivatives, which were attractive as organic materials, was also developed.

  • Research Products

    (11 results)

All 2009 2008 2007

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (6 results)

  • [Journal Article] Stereoselective Restrucuring of 3-Arylcyclobutanols into 1-Indanols by Sequential Breaking and Formation of Carbon-Carbon Bonds2009

    • Author(s)
      Masanori Shigeno, Taiga Yamamoto, Masahiro Murakami
    • Journal Title

      Chem. Eur. J. 15

      Pages: 12929-12931

    • Peer Reviewed
  • [Journal Article] Nickel-Catalysed Denitrogenative Alkyne Insertion Reaction of N-Sulfony1-1, 2, 3-triazoles2009

    • Author(s)
      Tomoya Miura, Motoshi Yamauchi, Masahiro Murakami
    • Journal Title

      Chem. Commun.

      Pages: 1470-1471

    • Peer Reviewed
  • [Journal Article] Nickel-Catlyzed [4+2+2]-Type Annulation Reaction of Cyclobutanones with Diynes and Enynes2008

    • Author(s)
      Shinji Ashida, Masahiro Murakami
    • Journal Title

      Bull. Chem. Soc. Jpn. 81

      Pages: 885-893

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Carbonylation of Spiropentanes2007

    • Author(s)
      Takanori Matsuda, Tomoya Tsuboi, Masahiro Murakami
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 12596-12597

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of 3, 4-Dihydrocoumarins by Rhodium-Catalyzed Reaction of 3-(2-Hydroxyphenyl)cyclobutanones2007

    • Author(s)
      Takanori Matsuda, Masanori Shigeno, Masahiro Murakami
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 12086-12087

    • Peer Reviewed
  • [Presentation] Enantioselective Carbon-Carbon Bond Cleavage: Rhodium-Catalyzed Restructuring of 3-Arylcyclobutanols into 1-Indanols2009

    • Author(s)
      Masahiro Murakami
    • Organizer
      Catalysis and Fine Chemicals 2009
    • Place of Presentation
      Korea University(韓国)
    • Year and Date
      2009-12-16
  • [Presentation] enantioselective synthesis of 1-indanols by rhodium-catalyzed activation of a carbon-carbon bond2009

    • Author(s)
      重野真徳, 山本泰河, 村上正浩
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学(京都)
    • Year and Date
      2009-09-10
  • [Presentation] ロジウム触媒による3-アリールシクロブタノールから1-インダノールへのエナンチオ選択的異性化反応2009

    • Author(s)
      山本泰河, 重野真徳, 村上正浩
    • Organizer
      日本化学会第89春季年会(2009)
    • Place of Presentation
      日本大学(千葉)
    • Year and Date
      2009-03-27
  • [Presentation] ロジウム触媒による炭素-炭素結合切断反応の合成化学的利用2008

    • Author(s)
      松田学則
    • Organizer
      日本化学会第88春季年会(2008)
    • Place of Presentation
      立教大学(東京)
    • Year and Date
      2008-03-27
  • [Presentation] Synthesis of (±)-β-Cuparenone via Rhodium-Catalyzed Carbonylation of Spiropentane2007

    • Author(s)
      Takanori Matsuda, Tomoya Tsuboi, Masahiro Murakami
    • Organizer
      14th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS14)
    • Place of Presentation
      奈良
    • Year and Date
      20070802-20070806
  • [Presentation] Rhodium-Catalyzed Asymmetric Synthesis of Lactones by Intramolecular Addition/Ring-Opening of Phenols to Cyclobutanones2007

    • Author(s)
      重野真徳, 松田学則, 村上正浩
    • Organizer
      第4回集積型合成国際シンポジウム(ISIS-4)
    • Place of Presentation
      滋賀
    • Year and Date
      2007-09-23

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Published: 2011-06-18   Modified: 2016-04-21  

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