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2011 Fiscal Year Final Research Report

An Efficient Access to Chiral Compounds via Asymmetric Hydrogenation of Polar Functional Groups

Research Project

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Project/Area Number 21550096
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKyushu University

Principal Investigator

ITO Masato  九州大学, 先導物質化学研究所, 准教授 (20293037)

Project Period (FY) 2009 – 2011
Keywords触媒設計・反応 / 不斉合成反応
Research Abstract

Novel molecular catalysts have been developed for the straightforward hydrogenation of a range of carboxylic acid derivatives under mild conditions. Modular design of chiral molecular catalysts could provide direct access to stereochemically well-defined moleculres, which might otherwise have required a detour to reach. Another important finding in this study is that the coexistence of inorganic base has led to dramatic improvement in their catalytic activity.

  • Research Products

    (27 results)

All 2011 2010 2009 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (14 results) Remarks (1 results) Patent(Industrial Property Rights) (2 results) (of which Overseas: 2 results)

  • [Journal Article] Catalytic Hydrogenation of Carboxamides and Esters by Well-Defined Cp^* Ru Complexes Bearing a Protic Amine Ligand2011

    • Author(s)
      Masato Ito, Takashi Ootsuka, Ryo Watari Akira Shiibashi, Akio Himizu, Takao Ikariya
    • Journal Title

      Journal of the American Chemical Society

      Volume: 113 Pages: 4240-4242

    • Peer Reviewed
  • [Journal Article] Regioselective Lactonization of Unsymmetrical 1, 4-Diols : An Efficient Access to Lactone Lignans2011

    • Author(s)
      Masato Ito, Akira Shiibashi, Takao Ikariya
    • Journal Title

      Chemical Communications

      Volume: 47 Pages: 2134-2136

    • Peer Reviewed
  • [Journal Article] of 2-Aminoethanethiolato-bridged Dinuclear Ru(hmb) Complexes(hmb=η^6-hexamethylbenzene): Mechanistic Consideration on Transfer Hydrogenation with Bifunctional[ RuCl_2(hmb)]_2/2-Aminoethanethiol Catalyst System2010

    • Author(s)
      (3)Masato Ito, Akira Watanabe, Yuji Shibata, Takao Ikariya, Synthesis and Reactivity
    • Journal Title

      Organometallics

      Volume: 29 Pages: 4584-4592

    • Peer Reviewed
  • [Journal Article] Highly Enantioselective Hydrogenative Desymmetrization of Bicyclic Imides Leading to Multiply Functionalized Chiral Cyclic Compounds2010

    • Author(s)
      Masato Ito, Chika Kobayashi, Akio Himizu, Takao Ikariya
    • Journal Title

      Journal of the American Chemical Society

      Volume: 132 Pages: 11414-11415

    • Peer Reviewed
  • [Journal Article] Bifunctional Triflylamide-Tethered Cp. Rh and Cp. Ir Complexes : A New Entry for Asymmetric Hydrogenation Catalysts2010

    • Author(s)
      Masato Ito, Yoshinori Endo, Noriko Tejima, Takao Ikariya
    • Journal Title

      Organometallics

      Volume: 29 Pages: 2397-2399

    • Peer Reviewed
  • [Journal Article] Synthesis and Structure of Protic Amine Tethered Rhodium(III) Peralkylcyclopentadienyl Complexes2010

    • Author(s)
      Masato Ito, Noriko Tejima, Masahiro Yamamura, Yoshinori Endo, Takao Ikariya
    • Journal Title

      Organometallics

      Volume: 29 Pages: 1886-1889

    • Peer Reviewed
  • [Journal Article] (η^6-arene) Ru^<II>/Chiral SN Ligand : A Novel Bifunctional Catalyst System for Asymmetric Transfer Hydrogenation of Aromatic Ketones2009

    • Author(s)
      Masato Ito, Yuji Shibata, Akira Watanabe, Takao Ikariya
    • Journal Title

      Synlett

      Pages: 1621-1626

    • Peer Reviewed
  • [Journal Article] A Convenient Method for the Synthesis of Protic 2-(Tertiary phosphino)-1-amines and Their Cp* RuCl Complexes2009

    • Author(s)
      Masato Ito, Akihide Osaku, Chika Kobayashi, Akira Shiibashi, Takao Ikariya
    • Journal Title

      Organometallics

      Volume: 28 Pages: 390-393

    • Peer Reviewed
  • [Journal Article] Hydrogenation of N-Acylcarbamates and N-Acylsulfonamides Catalyzed by a Bifunctional[ Cp* Ru(PN)] Complex2009

    • Author(s)
      Masato Ito, Lee Wei Koo, Akio Himizu, Chika Kobayashi, Ayaka Sakaguchi, Takao Ikariya
    • Journal Title

      Angewandte Chemie-International Edition

      Volume: 48 Pages: 1324-1327

    • Peer Reviewed
  • [Journal Article] of Novel(η^1 :η^6-Aminoalkylarene) Ru^<II> Complexes2009

    • Author(s)
      Masato Ito, Hiroko Komatsu, Yoshinori Endo, Takao Ikariya, Synthesis and Structure
    • Journal Title

      Chemistry Letters

      Volume: 38 Pages: 98-99

    • Peer Reviewed
  • [Presentation] 新型キラル分子触媒の高度設計2011

    • Author(s)
      伊藤正人
    • Organizer
      有機合成秋季講演会
    • Place of Presentation
      鹿児島大学
    • Year and Date
      2011-12-08
  • [Presentation] 新規トリフリルアミドテザー型Cp. Ru錯体の合成と反応性2011

    • Author(s)
      坂本直紀,遠藤慶徳,伊藤正人,碇屋隆雄
    • Organizer
      錯体化学会第61回討論会
    • Place of Presentation
      岡山理科大学
    • Year and Date
      2011-09-17
  • [Presentation] プロティックアミンキレート配位子を有するCp^* Ru錯体を用いたN-アリールカルボン酸アミドの水素化反応2011

    • Author(s)
      亘理龍,大塚隆史,伊藤正人,碇屋隆雄
    • Organizer
      日本化学会第5回関東支部大会
    • Place of Presentation
      東京農工大学小金井キャンパス
    • Year and Date
      2011-08-30
  • [Presentation] Ryo Watari, Takashi Ootsuka, Akira Shiibashi, Akio Himizu, Masato Ito, Hydrogenation of Esters and Carboxamides Promoted by Bifunctional Cp^* Ru Catalysts2011

    • Author(s)
      Ryo Watari, Takashi Ootsuka, Akira Shiibashi, Akio Himizu, Masato Ito, Takao Ikariya
    • Organizer
      16^<th> IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Shanghai, China
    • Year and Date
      2011-07-24
  • [Presentation] Catalytic Hydrogenation of Carboxylic Acid Derivatives2011

    • Author(s)
      Masato Ito
    • Organizer
      G-COE Symposium on Organic Chemistry in Fukuoka
    • Place of Presentation
      Fukuoka, Japan
    • Year and Date
      2011-02-26
  • [Presentation] デザイン型錯体分子触媒の開発2010

    • Author(s)
      伊藤正人
    • Organizer
      近未来新素材研究会第10回講演会
    • Place of Presentation
      九州大学
    • Year and Date
      2010-10-19
  • [Presentation] Molecular Catalysts for Straightforward Hydrogenation of Polarized Bonds2010

    • Author(s)
      Masato Ito
    • Organizer
      Asian Core Program
    • Place of Presentation
      National Taiwan University, Taiwan
    • Year and Date
      2010-01-23
  • [Presentation] Molecular Catalysts for Straightforward Hydrogenation of Polarized Bonds2010

    • Author(s)
      Masato Ito
    • Organizer
      Asian Core Program
    • Place of Presentation
      National Taiwan Normal University, Taiwan
    • Year and Date
      2010-01-22
  • [Presentation] Molecular Catalysts for Straightforward Hydrogenation of Polarized Bonds2010

    • Author(s)
      Masato Ito
    • Organizer
      Asian Core Program
    • Place of Presentation
      National Tsing Hua University, Taiwan
    • Year and Date
      2010-01-21
  • [Presentation] Molecular Design of Bifunctional Cp* Ru Catalysts for Asymmetric Synthesis2009

    • Author(s)
      Masato Ito
    • Organizer
      The 11^<th> International KYOTO conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2009-11-12
  • [Presentation] 機能性アミノテザーを有するRu, Rh, Ir錯体の構造とその触媒機能2009

    • Author(s)
      伊藤正人,遠藤慶徳,手島典子,碇屋隆雄
    • Organizer
      第104回触媒討論会
    • Place of Presentation
      宮崎大学工学部
    • Year and Date
      2009-09-30
  • [Presentation] Cp^* Ru(PN)触媒を用いたトリオール類の高選択的ラクトン化反応2009

    • Author(s)
      伊藤正人,大澤康子,椎橋彬,碇屋隆雄
    • Organizer
      第104回触媒討論会
    • Place of Presentation
      宮崎大学工学部
    • Year and Date
      2009-09-30
  • [Presentation] SNキレート配位子を有する非対称二核錯体の生成機構2009

    • Author(s)
      伊藤正人,渡邊章,柴田祐二,碇屋隆雄
    • Organizer
      錯体化学会第59回討論会
    • Place of Presentation
      長崎大学
    • Year and Date
      2009-09-26
  • [Presentation] Asymmetric Hydrogenation of Imides Catalyzed by Novel Cp^* Ru(PN) Complex2009

    • Author(s)
      Masato Ito, Akio Himizu, Chika Kobayashi, Takao Ikariya
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学
    • Year and Date
      2009-09-11
  • [Remarks] ホームページ

    • URL

      http://www.researcherid.com/rid/G-3690-2010

  • [Patent(Industrial Property Rights)] Practical Method for Reducing Amides and Lactams2010

    • Inventor(s)
      碇屋隆雄,伊藤正人,大塚隆史
    • Industrial Property Rights Holder
      東京工業大学・セントラル硝子
    • Industrial Property Number
      A1, WO2010/073974
    • Acquisition Date
      2010-07-01
    • Overseas
  • [Patent(Industrial Property Rights)] Practical Method for Reducing Esters and Lactones2010

    • Inventor(s)
      碇屋隆雄,伊藤正人,椎橋彬,大塚隆史
    • Industrial Property Rights Holder
      東京工業大学・セントラル硝子
    • Industrial Property Number
      A1, WO2010/004883
    • Acquisition Date
      2010-01-14
    • Overseas

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Published: 2013-07-31  

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