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Studies on the Transition Metal-Rare Earth Metal/Dinuclear Schiff Base Catalysts, Mechanistic Studies and Application to New Asymmetric Reactions

Research Project

Project/Area Number 20685008
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

MATSUNAGA Shigeki  東京大学, 大学院・薬学系研究科, 准教授 (50334339)

Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥25,610,000 (Direct Cost: ¥19,700,000、Indirect Cost: ¥5,910,000)
Fiscal Year 2010: ¥7,410,000 (Direct Cost: ¥5,700,000、Indirect Cost: ¥1,710,000)
Fiscal Year 2009: ¥8,190,000 (Direct Cost: ¥6,300,000、Indirect Cost: ¥1,890,000)
Fiscal Year 2008: ¥10,010,000 (Direct Cost: ¥7,700,000、Indirect Cost: ¥2,310,000)
Keywords触媒 / 不斉合成 / 不斉触媒 / サレン / 非天然アミノ酸 / 医薬品合成 / 希土類触媒 / シッフ塩基 / 複核錯体
Research Abstract

Characterization of hetero-dinuclear rare earth metal/transition metal Schiff base complexes, as well as their applications to various enantioselective reactions have been investigated. Catalytic asymmetric nitro-Mannich-type reactions, catalytic asymmetric α-addition of isocyanato esters to aldehydes, and so on have been successfully developed, leading to providing useful synthetic methods for chiral nitrogen-containing building blocks. Thus, the achievement can contribute for the efficient synthesis of pharmaceuticals.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (25 results)

All 2010 2009 2008 Other

All Journal Article (16 results) (of which Peer Reviewed: 16 results) Presentation (4 results) Remarks (4 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Heterobimetallic Transition Metal/Rare Earth Metal Bifunctional Catalysis: a Cu-SnrSchiff Base Complex for syn-Selective Catalytic Asymmetric Nitro-Mannich Reaction2010

    • Author(s)
      S. Handa, V. Gnanadesikan, S. Matsunaga, M Shibasaki
    • Journal Title

      J. Am Chem Soc

      Volume: 132(13) Issue: 13 Pages: 4925-4934

    • DOI

      10.1021/ja100514y

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asynmetric Vinylogous Mannich -type and Michael Reactions of an α, β-Unsaturated y Butyrolactam Under Dinuclear Nickel Catalysis2010

    • Author(s)
      N. E. Shepherd, FL Tanabe, Y. Xu, S. Matsunaga, M. Sibasaki
    • Journal Title

      J. Am Chem Soc

      Volume: 132(11) Issue: 11 Pages: 3666-3667

    • DOI

      10.1021/ja1002636

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis of 3-Aminooxindoles: Enantiofacial Selectivity Switch in Bimetallic vs Monometallic Schiff Base Catalysis2010

    • Author(s)
      S. Mouri, Z. Chen, H. Mitsunuma, M. Furutachi, S. Matsunaga and M. Shibasaki
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 132 Issue: 4 Pages: 1255-1257

    • DOI

      10.1021/ja908906n

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Heterobimetallic Transition Metal/Rare Earth Metal Bifunctional Catalysis : A Cu/Sm/Schiff Base Complex for Syn-Selective Catalytic Asymmetric Nitro-Mannich Reaction2010

    • Author(s)
      Handa, S; Gnanadesikan, V.; Matsunaga, S.; Shibasaki, M.
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 132 Pages: 4925-4934

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asymmetric Vinylogous Mannich-Type and Michael Reactions of an α,β-Unsaturated γ-Butyrolactam under Dinuclear Nickel Catalysis2010

    • Author(s)
      Shepherd, N.E.; Tanabe, H.; Xu, Y.; Matsunaga, S.; Shibasaki, M.
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 132 Pages: 3666-3667

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Heterobimetallic Ni/La-salan Complex for Catalytic Asymmetric Decarboxylative 1,4-Addition of Malonic Acid Half-Thioester2010

    • Author(s)
      Furutachi, M.; Mouri, S.; Matsunaga, S.; Shibasaki, M.
    • Journal Title

      Chem.Asian.J.

      Volume: 5 Pages: 2351-2354

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis of 3-Aminooxindoles : Enantiofacial Selectivity Switch in Bimetallic vs Monometallic Schiff Base Catalysis2010

    • Author(s)
      S.Mouri, Z.Chen, H.Mitsunuma, M.Furutachi, S.Matsunaga, M.Shibasaki
    • Journal Title

      J.Am.Chem.Soc. 132

      Pages: 1255-1257

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Contiguous Tetrasubstituted Chiral Carbon Stereocenters via Direct Catalytic Asymmetric Aldol Reaction of α-Isothiocyanato Esters to Ketones2009

    • Author(s)
      T. Yoshino, H. Morimoto, G. Lu, S. Matsunaga and M. Shibasaki
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 131 Issue: 47 Pages: 17082-17083

    • DOI

      10.1021/ja908571w

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Heterobimetallic Ga/Yb-Schiff Base Complex for Catalytic Asymmetric a-Addition of Isocyanides to Aldehydes2009

    • Author(s)
      H. Mihara, Y. Xu, N. E. Shepherd, S. Matsunaga, and M. Shibasaki
    • Journal Title

      J. Am Chem Soc

      Volume: 131(24) Issue: 24 Pages: 8384-8385

    • DOI

      10.1021/ja903158x

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Homodinuclear Mn(III)_2-Schiff Base Complex for Catalytic Asymmetric 1,4-Additions of Oxindoles to Nitroalkenes2009

    • Author(s)
      Y. Kato, M. Furutachi, Z. Chen, H. Mistunuma, S. Matsunaga and M. Shibasaki
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 131 Issue: 26 Pages: 9168-9169

    • DOI

      10.1021/ja903566u

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Stable Homodinuclear Biscobalt(III)-Schiff Base Complex for Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Alkynones2009

    • Author(s)
      Z. Chen, M. Furutachi, Y. Kato, S. Matsunaga and M. Shibasaki
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 48 Issue: 12 Pages: 2218-2220

    • DOI

      10.1002/anie.200805967

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Heterobimetallic Ga/Yb-Schiff Base Complex for Catalytic Asymmetric α-Addition of Isocyanides to Aldehydes2009

    • Author(s)
      H.Mihara, Y.Xu, N.E.Shepherd, S.Matsunaga, M.Shibasaki
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 8384-8385

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Homodinuclear Mn(III)_2-Schiff Base Complex for Catalytic Asymmetric 1, 4-Additions of Oxindoles to Nitroalkenes2009

    • Author(s)
      Y.Kato, M.Furutachi, Z.Chen, H.Mitsunuma, S.Matsunaga, M.Shibasaki
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 9168-9169

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Stable Homodinuclear Biscobalt(III)Schiff Base Complex for Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Alkynones2009

    • Author(s)
      Z. Chen, F. Makoto, Y. Kato, S. Matsunaga, M. Shibasaki
    • Journal Title

      Angew. Chem. Mt. Ed 48

      Pages: 2218-2220

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct antiSelective Catalytic Asymmetric Mannich-type Reactions of aKetoanilides for y-Amino Amides and Azetidine-2-amides Synthesis2009

    • Author(s)
      Y. Xu, G. Lu, S. Matsunaga, M. Shibasaki
    • Journal Title

      Angew. Chem. In t. Ed 48(印刷中)

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asymmetric Mannich-type Reaction of R-Keto Phosphonate Using a Dinuclear Ni_2-Schiff Base Complex2008

    • Author(s)
      Z. Chen, K. Yakura, S. Matsunaga, M. Shibasaki
    • Journal Title

      Org. Lett 10

      Pages: 3239-3242

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] Development of multimetallic asymmetric catalysisthrough chiral ligand design2009

    • Author(s)
      S. Matsunaga
    • Organizer
      第4回三井化学触媒科学国際シンポジウム
    • Place of Presentation
      カズサアカデミアホール(木更津)(受賞講演)
    • Year and Date
      2009-03-11
    • Related Report
      2010 Final Research Report
  • [Presentation] Development of multimetallic asymmetric catalysis through chiral ligand design2009

    • Author(s)
      S. Matsunaga
    • Organizer
      第4回三井化学触媒科学国際シンポジウム
    • Place of Presentation
      カズサアカデミアホール(木更津)
    • Year and Date
      2009-03-11
    • Related Report
      2008 Annual Research Report
  • [Presentation] 不斉配位子の設計に基づく多中心協奏機能不斉触媒の開発2009

    • Author(s)
      松永茂樹
    • Organizer
      第8回化学・材料研究セミナー
    • Place of Presentation
      九州大学理学部(箱崎キャンパス)
    • Year and Date
      2009-01-24
    • Related Report
      2008 Annual Research Report
  • [Presentation] Bimetallic Cooperative Asymmetric Catalysis for C-C Bond Formation; Green Chemistry For Catalytic C-C Bond Formation2008

    • Author(s)
      S. Matsunaga
    • Organizer
      USA -Japan Young Chemist Exchange
    • Place of Presentation
      University of Texas, Austin, USA(招待講演)
    • Year and Date
      2008-07-11
    • Related Report
      2010 Final Research Report
  • [Remarks]

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://www.f.u-tokyo.ac.jp/~kanai/index.html

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.f.u-tokyo.ac.jp/~kanai/index.html

    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://www.f.u-tokyo.ac.jp/~kanai/index.html

    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性ジマンガン錯体2009

    • Inventor(s)
      柴崎正勝、松永茂樹、加藤祐子、陳志華、古舘信
    • Industrial Property Rights Holder
      日産化学工業株式会社
    • Industrial Property Number
      2009-047245
    • Filing Date
      2009-02-27
    • Related Report
      2010 Final Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

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