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2010 Fiscal Year Final Research Report

Advanced Control of Catalytic Activity and Stereoselectivity in Catalytic Asymmetric Reactions

Research Project

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Project/Area Number 19105002
Research Category

Grant-in-Aid for Scientific Research (S)

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

Principal Investigator

HAYASHI Tamio  Kyoto University, 大学院・理学研究科, 教授 (00093295)

Research Collaborator SHIRAKAWA Eiji  京都大学, 大学院・理学研究科, 准教授 (70273472)
NISHIMURA Takahiro  京都大学, 大学院・理学研究科, 講師 (50335197)
SHINTANI Ryo  京都大学, 大学院・理学研究科, 助教 (50372561)
Project Period (FY) 2007 – 2010
Keywords触媒的不斉合成 / 遷移金属錯体触媒 / 不斉配位子 / キラルジエン配位子 / 触媒活性 / 不斉付加反応 / 不斉重合
Research Abstract

One of the most important subjects in studying asymmetric catalysis is development of new chiral ligands which have both high catalytic activity and high enantioselectivity. We have successfully developed an entirely new type of chiral ligands which have olefins as coordinating functionalities to metal catalysts. Among them, chiral diene ligands showed great performance in terms of both catalytic activity and enantioselectivity in rhodium- and iridium-catalyzed asymmetric carbon-carbon bond forming reactions.

  • Research Products

    (29 results)

All 2011 2010 2009 2008 2007 Other

All Journal Article (15 results) (of which Peer Reviewed: 15 results) Presentation (8 results) Book (5 results) Remarks (1 results)

  • [Journal Article] Rhodium-Catalyzed Asymmetric Arylation of N-Tosyl Ketimines.2010

    • Author(s)
      Shintani, R., Takeda, M., Tsuji, T., Hayashi, T.J.
    • Journal Title

      Am.Chem.Soc. 132

      Pages: 13168-13169

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Enantioselective 1, 6-Addition of Arylboronic Acids to Enynamides : Asymmetric Synthesis of Axially Chiral Allenylsilanes.2010

    • Author(s)
      Nishimura, T., Makino, H., Nagaosa, M., Hayashi, T.
    • Journal Title

      J.Am.Chem.Soc. 132

      Pages: 12865-12867

    • Peer Reviewed
  • [Journal Article] Asymmetric Cyclopropanation of Alkenes with Dimethyl Diazomalonate Catalyzed by Chiral Diene.Rhodium Complexes.2010

    • Author(s)
      Nishimura, T., Maeda, Y., Hayashi, T.
    • Journal Title

      Angew.Chem.Int.Ed. 49

      Pages: 7324-7327

    • Peer Reviewed
  • [Journal Article] Iridium/Chiral Diene-Catalyzed Asymmetric 1, 6-Addition of Arylboroxines to α,β,γ,δ-Unsaturated Carbonyl Compounds.2010

    • Author(s)
      Nishimura, T., Yasuhara, Y., Sawano, T., Hayashi, T.
    • Journal Title

      J.Am.Chem.Soc. 132

      Pages: 7872-7873

    • Peer Reviewed
  • [Journal Article] Chiral Tetrafluorobenzobarrelenes as Effective Ligands for Rhodium-Catalyzed Asymmetric 1, 4-Addition of Arylboroxines to β, β-Disubstituted α, β-Unsaturated Ketones.2010

    • Author(s)
      Shintani, R., Takeda, M., Nishimura, T., Hayashi, T.
    • Journal Title

      Angew.Chem.Int.Ed. 49

      Pages: 3969-3971

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Asymmetric Synthesis of Spirocarbocyles : Arylboron Reagents as Surrogates of 1, 2-Dimetalloarenes.2010

    • Author(s)
      Shintani, R., Isobe, S., Takeda, M., Hayashi, T.
    • Journal Title

      Angew.Chem.Int.Ed. 49

      Pages: 3795-3798

    • Peer Reviewed
  • [Journal Article] Chiral Tetrafluorobenzobarrelene Ligands for the Rhodium-Catalyzed Asymmetric Cycloisomerization of Oxygen-and Nitrogen-Bridged 1, 6-Enynes.2010

    • Author(s)
      Nishimura, T., Kawamoto, T., Nagaosa, M., Kumamoto, H., Hayashi, T.
    • Journal Title

      Angew.Chem.Int.Ed. 49

      Pages: 1638-1641

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to β-Phthaliminoacrylate Esters toward the Synthesis of β-Amino Acids.2010

    • Author(s)
      Nishimura, T., Wang, J., Nagaosa, M., Okamoto, K., Shintani, R., Kwong, F.-Y., Yu, W.-Y., Chan, A.S.C., Hayashi, T.
    • Journal Title

      J.Am.Chem.Soc. 132

      Pages: 464-465

    • Peer Reviewed
  • [Journal Article] Chiral Diene Ligands for Asymmetric Catalysis.2009

    • Author(s)
      Shintani, R., Hayashi, T.
    • Journal Title

      Aldrichimica Acta 42

      Pages: 31-38

    • Peer Reviewed
  • [Journal Article] Sodium Tetraarylborates as Effective Nucleophiles in the Rhodium/Diene-Catalyzed 1, 4-Addition to β, β-Disubstituted α, β-Unsaturated Ketones : Catalytic Asymmetric Construction of Quaternary Carbon Stereocenters.2009

    • Author(s)
      Shintani, R., Tsutsumi, Y., Nagaosa, M., Nishimura, T., Hayashi, T.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 13588-13589

    • Peer Reviewed
  • [Journal Article] Tuning the Chiral Environment of C_2-Symmetric Diene Ligands : Development of 3, 7-Disubstituted Bicyclo[3.3.1]nona-2, 6-dienes.2009

    • Author(s)
      Shintani, R., Ichikawa, Y., Takatsu, K., Chen, F.-X., Hayashi, T.
    • Journal Title

      J.Org.Chem. 74

      Pages: 869-873

    • Peer Reviewed
  • [Journal Article] Simple Chiral Diene Ligands Provide High Enantioselectivities in Transition-Metal-Catalyzed Conjugate Addition Reactions.2008

    • Author(s)
      Okamoto, K., Hayashi, T., Rawal, V.
    • Journal Title

      H.Org.Lett. 10

      Pages: 4387-4389

    • Peer Reviewed
  • [Journal Article] A Cationic Rhodium-Chiral Diene Complex as a High-Performance Catalyst for the Intramolecular Asymmetric [4+2] Cycloaddition of Alkyne-1, 3-Dienes.2007

    • Author(s)
      Shintani, R., Sannohe, Y., Tsuji, T., Hayashi, T.
    • Journal Title

      Angew.Chem.Int.Ed. 46

      Pages: 7277-7280

    • Peer Reviewed
  • [Journal Article] Organo[2-(hydroxymethyl)phenyl]dimethylsilanes as Mild and Reproducible Agents for Rhodium-Catalyzed 1, 4-Addition Reactions.2007

    • Author(s)
      Nakao, Y., Chen, J.-S., Imanaka, H., Hiyama, T., Ichikawa, Y., Duan, W.-L., Shintani, R., Hayashi, T.
    • Journal Title

      J.Am.Chem.Soc. 129

      Pages: 9137-9143

    • Peer Reviewed
  • [Journal Article] Chiral Phosphine.Olefin Ligands in the Rhodium-Catalyzed Asymmetric 1, 4-Addition Reactions.2007

    • Author(s)
      Duan, W.-L., Iwamura, H., Shintani, R., Hayashi, T.
    • Journal Title

      J.Am.Chem.Soc. 129

      Pages: 2130-2138

    • Peer Reviewed
  • [Presentation] Recent Advances in Rhodium-Catalyzed Asymmetric Addition Reactions2010

    • Author(s)
      林民生
    • Organizer
      The 1st North West Organic Chemistry Symposium
    • Place of Presentation
      Manchester, UK
    • Year and Date
      2010-07-06
  • [Presentation] Recent Advances in the Chiral Diene Ligands for Asymmetric Catalysis2009

    • Author(s)
      林民生
    • Organizer
      International Symposium on Catalysis and Fine Chemicals (C&FC 2009)
    • Place of Presentation
      Seoul, Korea
    • Year and Date
      2009-12-16
  • [Presentation] Recent Advances in the Chiral Diene Ligands for Asymmetric Catalysis2009

    • Author(s)
      林民生
    • Organizer
      16th European Symposium on Organic Chemistry (ESOC 2009)
    • Place of Presentation
      Prague, Czech Republic
    • Year and Date
      2009-07-16
  • [Presentation] Recent Advances in Rhodium-Catalyzed Asymmetric Addition Reactions2009

    • Author(s)
      林民生
    • Organizer
      41st National Organic Chemistry Symposium 2009
    • Place of Presentation
      Boulder, Colorado, USA
    • Year and Date
      2009-06-09
  • [Presentation] Recent Advances in the Rhodium-Catalyzed Asymmetric Carbon-Carbon Bond Formation2008

    • Author(s)
      林民生
    • Organizer
      57th Natural Products Gordon Research Conference
    • Place of Presentation
      Tilton, New Hampshire, USA
    • Year and Date
      2008-07-21
  • [Presentation] Recent Advances in the Rhodium-Catalyzed Asymmetric Carbon-Carbon Bond Formation2008

    • Author(s)
      林民生
    • Organizer
      Bristol Synthesis Meeting 2008
    • Place of Presentation
      Bristol, UK
    • Year and Date
      2008-04-15
  • [Presentation] 新しい不斉環境-キラルジエン配位子2008

    • Author(s)
      林民生
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学,東京
    • Year and Date
      2008-03-28
  • [Presentation] Chiral Diene Ligands for Catalytic Asymmetric Reactions2007

    • Author(s)
      林民生
    • Organizer
      The 24th Herbert C.Brown Lectures in Organic Chemistry
    • Place of Presentation
      Purdue Univ., Indiana, USA
    • Year and Date
      2007-04-21
  • [Book] Science of Synthesis, Stereoselective Synthesis 1-Stereoselective Reactions of Carbon-Carbon Double Bonds (Asymmetric Hydrosilylation of Carbon-Carbon Double Bonds.)(de Vries, J.G., Ed.) Vol.2010/72011

    • Author(s)
      Han, J.W., Hayashi, T.
    • Total Pages
      923-939
    • Publisher
      Thieme
  • [Book] Catalytic Asymmetric Conjugate Reractions (Rhodium-and Palladium-Catalyzed Asymmetric Conjugate Additions.)(Cordova, A., Ed.) Chap.12010

    • Author(s)
      Berthon, G., Hayashi, T.
    • Total Pages
      1-70
    • Publisher
      Wiley-VCH
  • [Book] Catalytic Asymmetric Synthesis, 3rd Ed. (Asymmetric Hydrosilylation of Carbon-Carbon Double Bonds and Related Reactions.)(Ojima, I., Ed.) Chap.92010

    • Author(s)
      Han, J.W., Hayashi, T.
    • Total Pages
      771-798
    • Publisher
      Wiley
  • [Book] New Frontiers in Asymmetric Catalysis (Ligand Design for C-C Bond Formation.)(Mikami, K., Lautens, M., Eds.)2007

    • Author(s)
      Shintani, R., Hayashi, T.
    • Total Pages
      59-100
    • Publisher
      Wiley-VCH
  • [Book] Comprehensive Organometallic Chemistry III (C-E Bond Formation through Asymmetric Hydrosilylation of Alkenes.)(Crabtree, R.H., Mingos, D.M.P., Eds.) Vol.102007

    • Author(s)
      Hayashi, T., Yamasaki, K.
    • Total Pages
      815-838
    • Publisher
      Elsevier
  • [Remarks] ホームページ等

    • URL

      http://kuchem.kyoto-u.ac.jp/orgchem/Scientific_Research_S.htm

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

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