• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to project page

2009 Fiscal Year Final Research Report

Construction of New Chiral Skeletons Using by Catalytic Cycloaddition

Research Project

  • PDF
Project/Area Number 19350052
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

SHIBATA Takanori  Waseda University, 理工学術院, 教授 (80265735)

Project Period (FY) 2007 – 2009
Keywords有機合成 / 遷移金属 / 錯体触媒
Research Abstract

Transition metal catalyzed-reactions realize efficient and useful synthetic transformations. In particular, transition metals with chiral ligands can induce high enantioselectivity, and various types of chiral skeletons can be synthesized. I have focused on the development of chiral transition metal-catalyzed cycloadditions in this project. For example, consecutive inter- and intramolecular [2+2+2] cycloadditions of two o-phenylene-tethered triynes provided highly enantioselective synthesis of chiral substituted tetraphenylenes. The present protocol is a new and facile approach to the construction of chiral tetraphenylene skeleton. We also reported the enantioselective synthesis of the tripodal cage-type compounds with planar chirality. Intramolecular [2+2+2] cycloaddition of branched triynes, where diyne and alkyne moieties were connected by 2-aminophenol linkage, gave tripodal cyclophanes with almost perfect enantioselectivity.

  • Research Products

    (38 results)

All 2010 2009 2008 2007 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (25 results) Remarks (1 results)

  • [Journal Article] Catalytic Enantioselective Synthesis of Chiral Tetraphenylenes : Consecutive Inter-and Intramolecular Cycloadditions of Two Triynes2009

    • Author(s)
      T.Shibata, T.Chiba, H.Hirashima, Y.Ueno, K.Endo
    • Journal Title

      Angew.Chem., Int.Ed. 48

      Pages: 8066-8069

    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of Chiral Tripodal Cage Compounds by [2+2+2] Cycloaddition of Branched Triynes2009

    • Author(s)
      T.Shibata, T.Uchiyama K.Endo
    • Journal Title

      Org.Lett. 11

      Pages: 3906-3908

    • Peer Reviewed
  • [Journal Article] Recent Advances in Enantioselective [2+2+2] Cycloaddition2008

    • Author(s)
      T.Shibata, K.Tsuchikama
    • Journal Title

      Org.Biomol.Chem. 6

      Pages: 1317-1323

    • Peer Reviewed
  • [Journal Article] 触媒的不斉付加環化反応によるキラル環状化合物の合成2008

    • Author(s)
      柴田高範、土釜恭直
    • Journal Title

      ファインケミカル 5

      Pages: 55-67

    • Peer Reviewed
  • [Journal Article] Iridium-Catalyzed Consecutive and Enantioselective [2+2+2] Cycloaddition of Tetraynes and Hexaynes for the Construction of Axially Chiral Biaryl System2008

    • Author(s)
      T.Shibata, S.Yoshida, Y.Arai, M.Otsuka, K.Endo
    • Journal Title

      Tetrahedron 64

      Pages: 821-830

    • Peer Reviewed
  • [Journal Article] Rh-Catalyzed Intermolecular and Enantioselective [4+2] Cycloaddition of 1,3-Dienes with Dimethyl Acetylenedicarboxylate2008

    • Author(s)
      T.Shibata, D.Fujiwara, K.Endo
    • Journal Title

      Org.Biomol.Chem. 6

      Pages: 464-467

    • Peer Reviewed
  • [Journal Article] Carbonylative and Hydrosilylative Carbocyclization of 1,5-Diynes for the Synthesis of Cyclic Dienones2008

    • Author(s)
      T.Shibata, N.Nakagawa, Y.Ueno, K.Endo
    • Journal Title

      Organometallics 27

      Pages: 1342-1344

    • Peer Reviewed
  • [Journal Article] Enantioselective Syntheses of Various Chiral Multicyclic Compounds with Quaternary Carbon Stereocenters by Catalytic Intramolecular Cycloaddition2008

    • Author(s)
      T.Shibata, Y.Tahara, K.Tamura, K.Endo
    • Journal Title

      J.Am.Chem.Soc. 130

      Pages: 3451-3457

    • Peer Reviewed
  • [Journal Article] Iridium-Catalyzed Enantioselective Formal [4+2] Cycloaddition of Biphenylene and Alkynes for the Construction of Axial Chirality2008

    • Author(s)
      T.Shibata, G.Nishizawa, K.Endo, K.Synlett
    • Journal Title

      Speciall issue

      Pages: 765-768

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Intramolecular Cycloaddition of Cyclopropene-Ynes Triggered by Carbon-Carbon bond Cleavage2008

    • Author(s)
      T.Shibata, S.Maekawa, K.Tamura
    • Journal Title

      Heterocycles 76

      Pages: 1261-1270

    • Peer Reviewed
  • [Journal Article] Highly Diastereo- and Enantioselective Construction of Both Central and Axial Chiralities by Rh-Catalyzed [2+2+2] Cycloaddition2008

    • Author(s)
      T.Shibata, M.Otomo, Y.Tahara, K.Endo
    • Journal Title

      Org.Biomol.Chem. 6

      Pages: 4296-4298

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Enantioselective [2+2+2] Cycloaddition of Diynes with Unfunctionalized Alkenes2007

    • Author(s)
      T.Shibata, A.Kawachi, M.Ogawa, Y.Kuwata, K.Tsuchikama, K.Endo
    • Journal Title

      Tetrahedron 63

      Pages: 12853-12859

    • Peer Reviewed
  • [Presentation] ジエンインの分子内[2+2+2]付加環化反応による連続する三不斉中心の創製2010

    • Author(s)
      大友麻由美・遠藤恆平・柴田高範
    • Organizer
      日本化学会第90春季年会(3F1-20)
    • Place of Presentation
      近畿大学
    • Year and Date
      20100300
  • [Presentation] 触媒的不斉[2+2+2]付加環化反応によるキラルテトラフェニレン骨格の構築2010

    • Author(s)
      千羽達也・平島裕之・遠藤恆平・柴田高範
    • Organizer
      3F1-2
    • Place of Presentation
      近畿大学
    • Year and Date
      20100300
  • [Presentation] 分子内[2+2+2]付加環化反応による三脚型かご型化合物のエナンチオ選択的合成2010

    • Author(s)
      内山理文・遠藤恆平・柴田高範
    • Place of Presentation
      近畿大学
    • Year and Date
      20100300
  • [Presentation] Enantioselective Construction of New Cyclic Chiral Skeletons Using [2+2+2] Cycloaddition2009

    • Author(s)
      柴田高範
    • Organizer
      Catalysis and Fine Chemicals 2009
    • Place of Presentation
      Soul, Korea(招待講演)
    • Year and Date
      20091200
  • [Presentation] [2+2+2]付加環化反応によるキラル多環状化合物のエナンチオ選択的合成2009

    • Author(s)
      柴田高範
    • Organizer
      The Symposium on Chiral Science & Technology : Mesochemistry & Chemical Wisdom
    • Place of Presentation
      早稲田大学
    • Year and Date
      20090900
  • [Presentation] Enantioselective construction of new chiral skeleton by [2+2+2] cycloaddition2009

    • Author(s)
      柴田高範
    • Organizer
      The 238th ACS National Meeting
    • Place of Presentation
      Washington, United States
    • Year and Date
      20090800
  • [Presentation] Chiral Ir and Rh Complex-Catalyzed Cycloaddition for the Synthesis of Chiral Multicyclic Compounds2009

    • Author(s)
      T.Shibata, K.Tsuchikama
    • Organizer
      15th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 15)
    • Place of Presentation
      Glasgow, Scotland
    • Year and Date
      20090700
  • [Presentation] Enantioselective Synthesis of Axially Chiral Polyaryls using Ir-catalyzed [2+2+2] Cycloaddition2009

    • Author(s)
      柴田高範
    • Organizer
      The Second Waseda-NTU Joint Symposium in Chemistry, Singapore
    • Place of Presentation
      Singapore(招待講演)
    • Year and Date
      20090300
  • [Presentation] 触媒的[2+2+2]付加環化反応を利用した中心不斉と軸不斉の同時創製2009

    • Author(s)
      大友麻由美・田原優樹・遠藤恆平・柴田高範
    • Organizer
      日本化学会第89春季年会日本大学(2F2-02)
    • Year and Date
      20090300
  • [Presentation] Ir-and Rh-catalyzed Enantioselective Cycloadditions2008

    • Author(s)
      柴田高範
    • Organizer
      008 Science Seminar
    • Place of Presentation
      WuXi PharmaTech Shanghai, China(招待講演)
    • Year and Date
      20080900
  • [Presentation] Ir-and Rh-catalyzed Enantioselective Cycloadditions2008

    • Author(s)
      柴田高範
    • Organizer
      SIOC seminar 2008, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences
    • Place of Presentation
      Shanghai, China(招待講演)
    • Year and Date
      20080900
  • [Presentation] Rh-Catalyzed Enantioselective Cycloaddition for the Synthesis of Chiral Multicyclic Compounds2008

    • Author(s)
      T.Shibata, Y.Tahara, K.Tamura, K.Endo
    • Organizer
      23th International Conference on Organometallic Chemistry (ICOMC23)
    • Place of Presentation
      Rennes, France
    • Year and Date
      20080700
  • [Presentation] Enantioselective Cycloaddition for the Synthesis of Chiral Multicyclic Compounds2008

    • Author(s)
      柴田高範
    • Organizer
      Taiwan-Japan International Symposium on Organic Chemistry and Molecular Science
    • Place of Presentation
      Taipei, Taiwan(招待講演)
    • Year and Date
      20080400
  • [Presentation] Enantioselective Cycloaddition for the Synthesis of Chiral Multicyclic Compounds2008

    • Author(s)
      柴田高範
    • Organizer
      1st International Workshop in Organic and Organometallic Chemistry
    • Place of Presentation
      Nagoya, Japan.(招待講演)
    • Year and Date
      20080300
  • [Presentation] Rh触媒を用いたジインとカルボニル化合物類とのヘテロ[2+2+2]付加環化反応2008

    • Author(s)
      吉浪雄亮・土釜恭直・芳田志穂・遠藤恆平・柴田高範
    • Organizer
      日本化学会第88春季年会(5H1-01)
    • Place of Presentation
      立教大学
    • Year and Date
      20080300
  • [Presentation] ジエンインを用いる分子内付加環化反応を利用した不斉四級炭素を有する光学活性環状化合物の合成2008

    • Author(s)
      田原優樹・田村耕平・遠藤恆平・柴田高範
    • Organizer
      日本化学会第88春季年会(5H1-16)
    • Place of Presentation
      立教大学
    • Year and Date
      20080300
  • [Presentation] エンジインを用いる分子内付加環化反応を利用した不斉四級炭素を有する光学活性環状化合物の合成2008

    • Author(s)
      田村耕平・田原優樹・遠藤恆平・柴田高範
    • Organizer
      日本化学会第88春季年会(5H1-17)
    • Place of Presentation
      立教大学
    • Year and Date
      20080300
  • [Presentation] ヘキサインの触媒的不斉[2+2+2]付加環化反応を利用した軸不斉大環状化合物の合成2008

    • Author(s)
      千羽達也・西澤豪・遠藤恆平・柴田高範
    • Organizer
      日本化学会第88春季年会(4H3-32)
    • Place of Presentation
      立教大学
    • Year and Date
      20080300
  • [Presentation] イリジウム触媒によるビフェニレンの炭素-炭素結合活性化を用いた軸不斉ビアリール化合物の合成2008

    • Author(s)
      西澤豪・遠藤恆平・柴田高範
    • Organizer
      日本化学会第88春季年会(4H3-33)
    • Place of Presentation
      立教大学
    • Year and Date
      20080300
  • [Presentation] Asymmetric Cycloaddition for the Synthesis of Chiral Cyclic Compounds2007

    • Author(s)
      柴田高範
    • Organizer
      The 17th Symposium on Optically Active Compounds, Yamada & Koga Prize
    • Place of Presentation
      Tokyo, Japan.(招待講演)
    • Year and Date
      20071100
  • [Presentation] 分子内付加環化反応を利用した不斉四級炭素を有する光学活性多環状化合物の合成2007

    • Author(s)
      田原優樹、田村耕平、柴田高範
    • Organizer
      第92回有機合成シンポジウム(O-2)
    • Place of Presentation
      早稲田大学
    • Year and Date
      20071100
  • [Presentation] Enantioselective [2+2+2] Cycloaddition as a Synthetic Tool2007

    • Author(s)
      柴田高範
    • Organizer
      IUPAC 3rd International Symposium on Novel Materials and Synthesis & 17th International Symposium on Fine Chemistry and Functional Polymers
    • Place of Presentation
      Shanghai, China(招待講演)
    • Year and Date
      20071000
  • [Presentation] Iridium-Catalyzed Enantioselective [2+2+2] Cycloaddition for the Synthesis of Axially Chiral Compounds2007

    • Author(s)
      柴田高範
    • Organizer
      4^<th> Japanese-Sino Symposium on Organic Chemistry for Young Scientists
    • Place of Presentation
      Narita, Japan(招待講演)
    • Year and Date
      20070900
  • [Presentation] Highly Enantioselective Intramolecular [2+2+2] Cycloaddition of Enediynes and Dienynes2007

    • Author(s)
      T.Shibata, Y.Tahara, K.Tamura
    • Organizer
      The 234th ACS National Meeting
    • Place of Presentation
      Boston, United States
    • Year and Date
      20070800
  • [Presentation] エナンチオ選択的[2+2+2]付加環化反応による軸不斉の創製2007

    • Author(s)
      柴田高範
    • Organizer
      モレキュラー・キラリティー2007
    • Place of Presentation
      東京理科大学
    • Year and Date
      20070500
  • [Remarks]

    • URL

      http://www.chem.waseda.ac.jp/shibata/

URL: 

Published: 2012-01-26   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi