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Catalytic Asymmetric Synthesis of Chiral Transition-Metal Complexes by the Use of Modern Organic Transformation

Research Project

Project/Area Number 24655039
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Inorganic chemistry
Research InstitutionHokkaido University

Principal Investigator

OGASAWARA Masamichi  北海道大学, 触媒化学研究センター, 准教授 (70301231)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords有機金属化学 / 触媒的不斉合成 / 均一系触媒 / 面不斉 / メタロセン / アレーンクロム / メタセシス / 有機合成 / 遷移金属錯体 / リン原子 / 中心不斉 / モリブデン / 軸不斉 / 金属中心不斉
Research Abstract

Kinetic resolution of 1,2-diallylferrocene derivatives by Mo-catalyzed asymmetric ring-closing metathesis (ARCM) gave the corresponding (4,7-dihydroindenyl)iron(II) derivatives in good yields with high enantioselectivity. In the same way, desymmetrization of (1,2,3-triallylindenyl)-metallocenes by ARCM provided the corresponding (1,4-dihydrofluorenyl)-metallocene derivatives in high ee's.
The Cs-symmetric zirconocenes could be converted to the corresponding C3-bridged planar-chiral ansa-zirconocenes by ARCM with high enantioselectivity. The obtained planar-chiral ansa-zirconocene complexes could be applicable to the asymmetric carbometallation reaction as catalysts.
Kinetic resolution of the racemic planar-chiral (arene)chromium complexes was realized by Mo-catalyzed ARCM with excellent enantioselectivity. The optically active (bromoarene)chromium complex thus obtained is an excellent precursor to various planar-chiral (arene)chromium complexes.

Report

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

    (32 results)

All 2014 2013 2012

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (21 results) (of which Invited: 3 results)

  • [Journal Article] Hybrid sponge comprised of galactosylated chitosan and hyaluronic acid mediates the co-culture of hepatocytes and endothelial cells2014

    • Author(s)
      Shang, Y., M. Tamai, R. Ishii, N. Nagaoka, Y. Yoshida, M. Ogasawara, J. Yang, Y. Tagawa
    • Journal Title

      J. Biosci. Bioeng.

      Volume: 117 Issue: 1 Pages: 99-106

    • DOI

      10.1016/j.jbiosc.2013.06.015

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Helically Chiral Diene in Asymmetric Catalysis: C2-Symmetric (Z,Z)-2,3-Bis[1-(diphenylphosphinyl)ethylidene]tetralin as Highly Active Lewis-Base Organocatalyst2013

    • Author(s)
      Ogasawara, M.; Kotani, S.; Nakajima, H.; Furusho, H.; Miyasaka, M.; Shimoda, Y.; Wu, W.-Y.; Sugiura, M.; Takahashi, T.; Nakajima, M.
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 51 Pages: 13798-13802

    • DOI

      10.1002/anie.201308112

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Aldol Reaction on Water Using an Organocatalyst Tethered on a Thermoresponsive Block Copolymer2013

    • Author(s)
      Noriyuki Suzuki, Takahiro Inoue, Takumi Asada, Ryuji Akebi, Go Kobayashi, Masahiro Rikukawa, Yoshiro Masuyama, Masamichi Ogasawara, Tamotsu Takahashi, San H. Thang
    • Journal Title

      Chemistry Letters

      Volume: 42 Issue: 12 Pages: 1493-1495

    • DOI

      10.1246/cl.130711

    • NAID

      130004867826

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Inter-versus Intraanular-Ring-Closing Metathesis of Polyallylferrocenes Ftye-Fold RCM within a Single Molecole2013

    • Author(s)
      Masamichi Ogasawara, Wei-Yi Wu, Sachie Arae, Kiyohiko Nakajima, Tamotsu Takahashi
    • Journal Title

      Organometallics

      Volume: 32 Issue: 21 Pages: 6593-6598

    • DOI

      10.1021/om400936b

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Morita-Baylis-Hillman Reaction Catalyzed by a Chiral Phosphine Oxide2013

    • Author(s)
      Kotani, S.; Ito, M.; Nozaki, H.; Sugiura, M.; Ogasawara, M.; Nakajima, M.
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 48 Pages: 6430-6433

    • DOI

      10.1016/j.tetlet.2013.09.067

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Benzo[b]phosphaferrocene Derivatives2013

    • Author(s)
      Ogasawara, Masamichi; Arae, Sachie; Watanabe, Susumu; Subbarayan, Velusamy; Sato, Hiroyasu; Takahashi, Tamotsu
    • Journal Title

      Organometallics

      Volume: 32(17) Issue: 17 Pages: 4997-5000

    • DOI

      10.1021/om400496b

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Kioetio Resolution of Planar-Chiral,1,2-Disuhsrituted Fetroones by Molybdenum-Caralyzed Asymmetric Iutraanular Ring-Cloeing Metafhesis2013

    • Author(s)
      Masamichi Ogasawara, Sachie Arae, Susumu Watanabe, Kiyohiko Nakajima, Tamotsu Takahashi
    • Journal Title

      Chemistry-A European Journel

      Volume: 19 Issue: 13 Pages: 4151-4154

    • DOI

      10.1002/chem.201300116

    • Related Report
      2013 Annual Research Report 2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Preparation of C2-Symmetric Allenes by Palladium-Catalyzed Double-Nucleophilic Substitution on 3-Bromopenta-2,4-dienyl Acetate2012

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

      Journal of Organic Chemistry

      Volume: 77 Issue: 12 Pages: 5406-5410

    • DOI

      10.1021/jo300511e

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Kinetic Resolution of Planar-Chiral (h6-Arene)chromium Complexes by Molybdenum-Catalyzed
Asymmetric Ring-Closing Metathesis2012

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

      Angew. Chem. Int. Ed.

      Volume: 51 Issue: 12 Pages: 2951-2955

    • DOI

      10.1002/anie.201108292

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Effects of Silyl Substituents on the Palladium-Catalyzed Asymmetric Synthesis of Axially Chiral (Allenylmethy1)silanes and Their SE2 Chirality Transfer Reactions2012

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

      European Journal of Organic Chemistry

      Volume: 2012 Issue: 8 Pages: 1656-1663

    • DOI

      10.1002/ejoc.201101634

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis of Planar-Chiral Transition-Metal Complexes2012

    • Author(s)
      荒江祥永・小笠原正道
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 70 Issue: 6 Pages: 593-605

    • DOI

      10.5059/yukigoseikyokaishi.70.593

    • NAID

      10030765844

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Presentation] Catalytic Enantioselective Synthesis of Planar-Chiral (η^6-Arene)chromium Complexes2014

    • Author(s)
      Ogasawara, M.
    • Organizer
      The 247th ACS National Meeting, Dallas
    • Place of Presentation
      TX, USA
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Enantioselective Synthesis of Planar-Chiral (η6-Arene)chromium Complexes2014

    • Author(s)
      Masamichi Ogasawara
    • Organizer
      The 247th ACS National Meeting
    • Place of Presentation
      Dallas Convention Center (USA)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Atropisomeric Chiral Dienes in Asymmetric Catalysis : Design, Synthesis, and Application of C_2-Symmetric (Z,Z)-1,2-Bis[1-(diphenylphosphino)ethylidene]c ycloalkane Derivatives2013

    • Author(s)
      Ogasawara, M.
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2013 (C&FC 2013)
    • Place of Presentation
      Renmin University of China, Beijing, China
    • Related Report
      2013 Final Research Report
  • [Presentation] 新規不斉有機分子触媒ライブラリーの構築2013

    • Author(s)
      小笠原正道
    • Organizer
      日本プロセス化学会2013ウインターシンポジウム
    • Place of Presentation
      日本プロセス化学会、仙台市民会館(仙台市)
    • Related Report
      2013 Final Research Report
  • [Presentation] Palladium-Catalyzed Asymmetric Synthesis of Axially Chiral Allenes and Application to Synthesis of Allenic Natural Products2013

    • Author(s)
      Ogasawara, M.
    • Organizer
      The 48th Advances in Organic, Bioorganic and Pharmaceutical Chemistry (Liblice 2013)
    • Place of Presentation
      Harmony Hotel,Špindlerův Mlýn, Czech Republic
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Enantioselective Synthesis of Planar-Chiral (π-Arene)chromium Complexes2013

    • Author(s)
      Ogasawara, M
    • Organizer
      The 4th UK/Japan Conference in Catalytic Asymmetric Synthesis
    • Place of Presentation
      Sendai International Center, Sendai, Japan
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Enantioselective Synthesis of Planar-Chiral Transition-Metal Complexes2013

    • Author(s)
      Ogasawara, M
    • Organizer
      The 245th ACS National Meeting
    • Place of Presentation
      The 245th ACS National Meeting
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Asymmetric Synthesis of Planar-Chiral Ferrocenes and Their Applications in Optically Active Metallocene-Polymers2013

    • Author(s)
      Ogasawara, M
    • Organizer
      The 3rd Molecular Materials Meeting (M3)
    • Place of Presentation
      Singapore, Singapore
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Enantioselective Synthesis of Planar-Chiral Transition-Metal Complexes2013

    • Author(s)
      Masamichi Ogasawara
    • Organizer
      The 245th ACS National Meeting
    • Place of Presentation
      New Orleans Convention Center (USA)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Catalytic Enantioselective Synthesis of Planar-Chiral (π-Arene)chromium Complexes2013

    • Author(s)
      Masamichi Ogasawara
    • Organizer
      The 4th UK/Japan Conference in Catalytic Asymmetric Synthesis
    • Place of Presentation
      仙台国際センター(仙台市)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Catalytic Enantioselective Synthesis of Planar-Chiral (π-Arene)chromium Complexes by Asymmetric RCM2013

    • Author(s)
      Masamichi Ogasawara
    • Organizer
      ISOM-XX
    • Place of Presentation
      奈良東大寺講堂(奈良市)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Catalytic Induction of Planar Chirality in Functional Metallocenes by Mo-Catalyzed Asymmetric Ring-Closing Metathesis2013

    • Author(s)
      Masamichi Ogasawara, Sachie Arae, Susumu Watanabe, Ayaka Oana, Kiyohiko Nakajima, Tamotsu Takahashi
    • Organizer
      ISOM-XX
    • Place of Presentation
      奈良東大寺講堂(奈良市)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Design and Synthesis of Phosphine-Olefin Ligands Having Planar-Chiral (π-Arene)chromium Framework and Application in Asymmetric Catalysis2013

    • Author(s)
      Masamichi Ogasawara, Wei-Yi Wu, Takeshi Nakaya, Tomotaka Morita, Sachie Arae, Ya-Yi Tseng, Tamotsu Takahashi, Ken Kamikawa
    • Organizer
      ISOM-XX
    • Place of Presentation
      奈良東大寺講堂(奈良市)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Catalytic Enantioselective Synthesis of Planar-Chiral Zirconocenes and Their Application as Chiral Catalysts2013

    • Author(s)
      Masamichi Ogasawara, Sachie Arae, Ayaka Oana, Wei-Yi Wu, Kiyohiko Nakajima, Tamotsu Takahashi
    • Organizer
      60th Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      学習院大学(東京・目黒区)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 不斉閉環メタセシス反応によるジヒドロインデニル構造を有する面不斉錯体の触媒的不斉合成2013

    • Author(s)
      小笠原正道、荒江 祥永、中島 清彦、高橋 保
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(草津市)
    • Related Report
      2012 Research-status Report
  • [Presentation]2012

    • Author(s)
      Ogasawara, M
    • Organizer
      Visiting Lecturer of the Chemistry Research Promotion Center (Taiwan)
    • Place of Presentation
      National Science Council, Taiwan
    • Related Report
      2013 Final Research Report
  • [Presentation] Herically Chiral Dienes in Asymmetric Catalysis : C_2-Symmetric (Z, Z)-1,2-Bis(1-diphenylphosphinylethylidene)cyclo hexanes as Highly Acitve Lewis-Base Organocatalysts2012

    • Author(s)
      Ogasawara, M
    • Organizer
      The 1st Japan-USA Organocatalytic Symposium
    • Place of Presentation
      Honolulu, HI, USA
    • Related Report
      2013 Final Research Report
  • [Presentation] Design and Synthesis of Phosphine-Olefin Ligands Having Planar-Chiral (π-Arene)chromium Framework and Application in Asymmetric Catalysis2012

    • Author(s)
      Ogasawara, M
    • Organizer
      Cambodian Malaysian Chemical Conference
    • Place of Presentation
      Siem Reap, Cambodia
    • Related Report
      2013 Final Research Report
  • [Presentation] Helically Chiral Dienes in Asymmetric Catalysis : Design, Synthesis, and Application of 1,4-Bis(phosphino)-1,3-butadiene Derivatives Having C2-C3-Fused Cyclic System2012

    • Author(s)
      Ogasawara, M
    • Organizer
      The 17th Malaysian Chemical Congress
    • Place of Presentation
      Kuala Lumpur, Malaysia
    • Related Report
      2013 Final Research Report
  • [Presentation] Design and Synthesis of Phosphine-Olefin Ligands Having Planar-Chiral (π-Arene)chromium Framework and Application in Asymmetric Catalysis2012

    • Author(s)
      Masamichi Ogasawara, Tomotaka Morita, Takeshi Nakaya, Ya-Yi Tseng, Sachie Arae, Wei-Yi Wu, Tamotsu Takahashi, Ken Kamikawa
    • Organizer
      59th Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      大阪大学(大阪府)
    • Related Report
      2012 Research-status Report
  • [Presentation] Catalytic Enantioselective Synthesis of Axially Chiral N-Aryl Indole Chromium Complex by Molybdenum-Catalyzed Asymmetric Desymmetrization2012

    • Author(s)
      Ken Kamikawa, Sachie Arae, Wei-Yi Wu, Chihiro Nakamura, Tamotsu Takahashi, Masamichi Ogasawara
    • Organizer
      59th Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      大阪大学(大阪府)
    • Related Report
      2012 Research-status Report

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

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