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Development of base metal catalyst bearing N4 and PNN ligand toward asymmetric hydrogenation

Research Project

Project/Area Number 15K13693
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionNagoya University

Principal Investigator

Kitamura Masato  名古屋大学, 創薬科学研究科, 教授 (50169885)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords卑金属触媒 / 卑金属 / 不斉水素化
Outline of Final Research Achievements

Asymmetric hydrogenation is one of the reliable and practical tools to provide chiral materials. Starting from development of Noyori hydrogenation using Ru complex, this chemistry has been highly sophisticated to be nearly perfect reaction up to now. Under this stream, replacement of rare metals with base metals is an important subject from the view points of resources, cost, and safety. We have aimed to solve this problem on the basis of non-phosphine-type complex catalyst. We have developed two representative ligands, Ph-BINAN-H-Py and R-BINAN-Ph-PPh2, the Ru complexes of which show high performance in asymmetric hydrogenation of ketones. In this study, a series of base metal complexes of these ligands have been synthesized and their structures have been elucidated, establishing a basis for the future screening of base complexes.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • Research Products

    (14 results)

All 2017 2016 2015

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (3 results) (of which Invited: 2 results)

  • [Journal Article] Enantio- and Diastereoselective Dehydrative “One-Step” Construction of Spirocarbocycles via a Ru/H+-Catalyzed Tsuji-Trost Approach2017

    • Author(s)
      Yusuke Suzuki, Namdev Vatmurge, Shinji Tanaka, Masato Kitamura
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 12 Issue: 6 Pages: 633-637

    • DOI

      10.1002/asia.201700013

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of an Axially Chiral sp3P/sp3NH/sp2N-Combined Linear Tridentate Ligand―fac-Selective Formation of Ru(II) Complexes and Application to Ketone Hydrogenation
2016

    • Author(s)
      Tomoya Yamamura, Satoshi Nakane, Yuko Nomura, Shinji Tanaka, Masato Kitamura*
    • Journal Title

      Tetrahedron

      Volume: 未定 Issue: 26 Pages: 3781-3789

    • DOI

      10.1016/j.tet.2016.02.007

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of a Divergent Synthetic Route to the Erythrina Alkaloids: Asymmetric Syntheses of 8-Oxo-erythrinine, Crystamidine, 8-Oxo-erythraline, and Erythraline2016

    • Author(s)
      Hirotatsu Umihara, Tomomi Yoshino, Jun Shimokawa, Masato Kitamura, Tohru Fukuyama
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 55 Issue: 24 Pages: 6915-6918

    • DOI

      10.1002/anie.201602650

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Total Synthesis of (+)-Hinckdentine A via a Catalytic Dearomatization Approach2016

    • Author(s)
      Kazuya Douki, Hiroyuki Ono, Tohru Taniguchi, Jun Shimokawa, Masato Kitamura, Tohru Fukuyama
    • Journal Title

      Journal of the American Chemical Society

      Volume: 138 Issue: 44 Pages: 14578-14581

    • DOI

      10.1021/jacs.6b10237

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of an axially chiral sp3P/sp3NH/sp2N-combined linear tridentate ligand―fac-Selective formation of Ru(II) complexes and application to ketone hydrogenation2016

    • Author(s)
      Yamamura, T.; Nakane, S.; Nomura, Y.; Tanaka, S.; Kitamura, M.
    • Journal Title

      Tetrahedron

      Volume: 000 Pages: 000-000

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereochemical Stability Differences between Axially Chiral 6-Aryl-substituted Picolinic Esters and Their Benzoic Ester Derivatives: sp2N: vs sp2CH in CH3, C6H5, and CH3O ortho-Substitution Effect2015

    • Author(s)
      Tanaka, S.; Suzuki, Y.; Matsushita, M.; Kitamura, M.
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 88 Pages: 1726-1734

    • NAID

      130005113802

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Intramolecular Tsuji-Trost-type Allylation of Carboxylic Acids: Asymmetric Synthesis of Highly π-Allyl Donative Lactones2015

    • Author(s)
      Suzuki, Y.; Seki, T.; Tanaka, S.; Kitamura, M.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Pages: 9539-9542

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Catalytic Dehydrogenative N-((Triisopropylsilyl)oxy)carbonyl (Tsoc) Protection of Amines Using iPr3SiH and CO22015

    • Author(s)
      Tanaka, S.; Yamamura, T.; Nakane, S.; Kitamura, M.
    • Journal Title

      Chem. Commun.

      Volume: 51 Pages: 13110-13112

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Mechanism of Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by a Combined System of Ru(π-CH2C(CH3)CH2)2(cod) and the Chiral sp2N/sp3NH Hybrid Linear N4 Ligand Ph-BINAN-H-Py2015

    • Author(s)
      Nakatsuka, H.; Yamamura, T.; Shuto, Y.; Tanaka, S.; Yoshimura, M.; Kitamura, M.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Pages: 8138-8149

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Soft Ruthenium and Hard Bronsted Acid Combined Catalyst for Efficient Cleavage of Allyloxy Bonds. Application to Protecting Group Chemistry2015

    • Author(s)
      Tanaka, S.; Suzuki, Y.; Saburi, H.; Kitamura, M.
    • Journal Title

      Tetrahedron

      Volume: 71 Pages: 6559-6568

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Donor-Acceptor Bifunctional Molecular Catalyst: Its Development, Application, and Analysis,2015

    • Author(s)
      Kitamura, M.; Tanaka, S.; Yoshimura, M.
    • Journal Title

      J. Synth. Org. Chem., Jpn.

      Volume: 73 Pages: 690-700

    • NAID

      130005093742

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] ビスアミジン型sp2N系二座配位子の開発2016

    • Author(s)
      北村雅人
    • Organizer
      講演会
    • Place of Presentation
      東京工業大学
    • Year and Date
      2016-09-18
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] ヒンクデンチンAの不斉全合成2016

    • Author(s)
      道木和也、小野裕之、下川 淳、福山 透、北村雅人
    • Organizer
      第58回天然有機化合物討論会
    • Place of Presentation
      東北大学
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] アリル化・脱アリル化―ルテニウム/ブレンステッド酸 混合触媒―2016

    • Author(s)
      北村雅人
    • Organizer
      講演会「有機金属化学の大潮流」
    • Place of Presentation
      分子科学研究所
    • Year and Date
      2016-09-02
    • Related Report
      2016 Annual Research Report
    • Invited

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Published: 2015-04-16   Modified: 2018-03-22  

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