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2010 Fiscal Year Final Research Report

Development and Application of Methods for Catalytic Asymmetric Synthesis of Planar-Chiral Metallocene Complexes

Research Project

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Project/Area Number 20200051
Research Category

Grant-in-Aid for Scientific Research on Innovative Areas (Research a proposed research project)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Organic industrial materials
Research InstitutionHokkaido University

Principal Investigator

OGASAWARA Masamichi  Hokkaido University, 触媒化学研究センター, 准教授 (70301231)

Project Period (FY) 2008 – 2010
Keywordsメタロセン / 不斉合成 / 面不斉 / 均一系触媒 / 有機金属錯体 / 遷移金属触媒 / 光学活性 / メタセシス
Research Abstract

As shown in various planar-chiral metallocenylphosphine ligands, transition-metal complexes with planar chirality are useful chiral templates and have been utilized in asymmetric synthesis as chiral catalysts and chiral reagents. In spite of their usefulness, catalytic asymmetric reactions of preparing such planar-chiral compounds have bee extremely rare. In this research project, we have succeeded to develop various novel protocols of catalytically preparing planar-chiral metallocene derivatives in high enantiomeric purity. The methods we have developed include kinetic resolution of racemic planar-chiral metallocenes as well as asymmetric desymmetrization of planar-prochiral phosphaferrocenes. We have also demonstrated that our methods can be applicable to kinetic resolution of planar-chiral (η^6-arene)chromium complexes, indicating potential versatility of the protocols.

  • Research Products

    (20 results)

All 2011 2010 2009 2008 Other

All Journal Article (13 results) (of which Peer Reviewed: 13 results) Presentation (5 results) Book (2 results)

  • [Journal Article] Preparation of Osmium- 5-Phospholide Complexes and Their Reactions with Acyl Electrophiles : C=O Bond Cleavage and C-C Bond Formation within Metal-Coordination Sphere2011

    • Author(s)
      Ogasawara, M., Shintani, M., Watanabe, S., Sakamoto, T., Nakajima, K., Takahashi, T.
    • Journal Title

      Organometallics 30

      Pages: 1487-1492

    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of Planar-Chiral Phosphaferrocenes by Molybdenum-Catalyzed Asymmetric Interannular Ring-Closing Metathesis2010

    • Author(s)
      Ogasawara, M., Watanabe, S., Nakajima, K., Takahashi, T.
    • Journal Title

      J.Am.Chem.Soc. 132

      Pages: 2136-2137

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Asymmetric Synthesis of Axially Chiral Allenylsilanes and Their Application to S_E2' Chirality Transfer Reactions2010

    • Author(s)
      Ogasawara, M., Okada, A., Subbarayan, V., Sorgel, S., Takahashi, T.
    • Journal Title

      Org.Lett. 12

      Pages: 5736-5739

    • Peer Reviewed
  • [Journal Article] Synthesis of Fluorinated Allenes via Palladium-Catalyzed Monofluoromethylation Using FBSM2009

    • Author(s)
      Ogasawara, M., Murakami, H., Furukawa, T., Takahashi, T., Shibata, N.
    • Journal Title

      Chem.Commun.

      Pages: 7366-7368

    • Peer Reviewed
  • [Journal Article] Unusual Transposition of Allenic Framework in Intramolecular Cyclization of Acetal-Tethered (Allenylmethyl)silanes2009

    • Author(s)
      Ogasawara, M., Okada, A., Murakami, H., Watanabe, S., Ge, Y., Takahashi, T.
    • Journal Title

      Org.Lett. 11

      Pages: 4240-4243

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Synthesis of Endocyclic Allenes and Their Application in Stereoselective [2+2]Cycloaddition with Ketenes2009

    • Author(s)
      Ogasawara, M., Okada, A., Nakajima, K., Takahashi, T.
    • Journal Title

      Org.Lett. 11

      Pages: 177-180

    • Peer Reviewed
  • [Journal Article] Catalytic Enantioselective Synthesis of Axially Chiral Allenes2009

    • Author(s)
      Ogasawara, M.
    • Journal Title

      Tetrahedron:Asymmetry 20

      Pages: 259-271

    • Peer Reviewed
  • [Journal Article] Transition-Metal-Catalyzed Enantioselective Synthesis of Compounds with Non-Centrochirality2009

    • Author(s)
      Ogasawara, M., Watanabe, S.
    • Journal Title

      Synthesis

      Pages: 1761-1785,3177-3178

    • Peer Reviewed
  • [Journal Article] メタセシス反応を用いる面不斉メタロセン類の立体選択的合成法の開発2009

    • Author(s)
      小笠原正道・渡邉進
    • Journal Title

      触媒 51

      Pages: 583-587

    • Peer Reviewed
  • [Journal Article] Preparation of [4]- and [5]Ferrocenophanes by Ruthenium-Catalyzed Ring-Closing Ene-Yne Metathesis2008

    • Author(s)
      Ogasawara, M., Watanabe, S., Nakajima, K., Takahashi, T.
    • Journal Title

      Organometallics 27

      Pages: 6565-6569

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Planar-Chiral Ferrocenes by Mo- or Ru-Catalyzed Enantioselective Metathesis2008

    • Author(s)
      Ogasawara, M., Watanabe, S., Nakajima, K., Takahashi, T.
    • Journal Title

      Pure Appl.Chem. 80

      Pages: 1109-1113

    • Peer Reviewed
  • [Journal Article] パラジウム錯体触媒による置換アレン類の立体選択的合成法の開発とその応用2008

    • Author(s)
      小笠原正道
    • Journal Title

      有機合成化学協会誌 66

      Pages: 100-109

    • Peer Reviewed
  • [Journal Article] Ring-Closing Metathesis within Chromium-Coordination Sphere : Facile Access to Phosphine-Chelate (π-Arene)chromium Complexes

    • Author(s)
      Ogasawara, M., Wu, W.-Y., Arae, S., Morita, T., Watanabe, S., Takahashi, T., Kamikawa, K.
    • Journal Title

      J.Organomet.Chem. in press

    • Peer Reviewed
  • [Presentation] Catalytic Enantioselective Synthesis of Planar-Chiral Transition-Metal Complexes2011

    • Author(s)
      Ogasawara, M.
    • Organizer
      Third UK/Japan Conference in Catalytic Asymmetric Synthesis, Oxford University
    • Place of Presentation
      Oxford, United Kingdam
    • Year and Date
      20110614-20110616
  • [Presentation] Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis of 1,1'-Diallylmetallocenes : Catalytic Asymmetric Synthesis of Planar-Chiral Metallocenes2010

    • Author(s)
      Ogasawara, M.
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
    • Place of Presentation
      the Hilton Hotel, Honolulu, USA
    • Year and Date
      20101215-20101220
  • [Presentation] 均一系触媒による非中心不斉の立体制御-軸不斉アレンと面不斉メタロセンのエナンチオ選択的合成法の開発と応用2010

    • Author(s)
      小笠原正道
    • Organizer
      有機合成化学協会東北支部・春の講演会
    • Place of Presentation
      東北大学(仙台市)
    • Year and Date
      2010-07-03
  • [Presentation] Catalytic Asymmetric Synthesis of Planar-Chiral Metallocenes2009

    • Author(s)
      Ogasawara, M.
    • Organizer
      65th Southwest Regional Meeting of the American Chemical Society
    • Place of Presentation
      the Camino Real Hotel, El Paso, USA
    • Year and Date
      20091104-20091107
  • [Presentation] 面不斉メタロセンの触媒的不斉合成と光学活性メタロセン・ポリマー合成への応用2008

    • Author(s)
      小笠原正道
    • Organizer
      京都大学グローバルCOE有機若手ワークショップ、京都大学グローバルCOEプログラム
    • Place of Presentation
      京都大学大学院理学研究科(京都市)
    • Year and Date
      20080911-20080912
  • [Book] 合成有機化学 反応機構によるアプローチ(原著:Parashar, R.K.Reaction Mechanisms in Organic Synthesis, Wiley Interscience)2011

    • Author(s)
      柴田高範・小笠原正道・鹿又宣弘・斉藤慎一・庄司満訳
    • Total Pages
      436
    • Publisher
      東京化学同人
  • [Book] Compounds with All-Carbon Functions : Cumulenes and Allenes(Product Class 1 : Cumulenes In Science of Synthesis, Houben-Weyl, Methods of Molecular Transformations : Vol. 44)(Krause, N., ed.)2008

    • Author(s)
      Ogasawara, M.
    • Total Pages
      9-70
    • Publisher
      Georg Thieme Verlag : Stuttgart

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Published: 2012-02-13   Modified: 2016-04-21  

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