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Catalytic Asymmetric Hydrogenation of Polycyclic Aromatic Compounds

Research Project

Project/Area Number 19685008
Research Category

Grant-in-Aid for Young Scientists (A)

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

Principal Investigator

KUWANO Ryoichi  Kyushu University, 大学院・理学研究院, 教授 (20273477)

Project Period (FY) 2007 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥25,610,000 (Direct Cost: ¥19,700,000、Indirect Cost: ¥5,910,000)
Fiscal Year 2009: ¥7,150,000 (Direct Cost: ¥5,500,000、Indirect Cost: ¥1,650,000)
Fiscal Year 2008: ¥7,540,000 (Direct Cost: ¥5,800,000、Indirect Cost: ¥1,740,000)
Fiscal Year 2007: ¥10,920,000 (Direct Cost: ¥8,400,000、Indirect Cost: ¥2,520,000)
Keywords触媒的不斉合成 / 水素化 / 芳香族化合物 / ナフタレン / キノリン / 光学活性化合物 / ルテニウム / テトラリン / 5.6.7.8-テトラヒドロキノリン
Research Abstract

Hydrogenations of 2,6- or 2,7-disubstituted naphthalenes proceeded in high yields with high enantioselectivity in the presence of the ruthenium complex which was chelated with the optically active bisphosphine, PhTRAP. The catalytic asymmetric hydrogenation produced optically active tetralines with up to 92% ee. The chiral ruthenium catalyst is also effective for the hydrogenation of quinolines to give 5,6,7,8-tetrahydroquinolines selectively. The asymmetric hydrogenation proceeded with up to 84% ee.

Report

(4 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Research Products

    (39 results)

All 2010 2009 2008 2007 Other

All Journal Article (20 results) (of which Peer Reviewed: 20 results) Presentation (15 results) Book (3 results) Remarks (1 results)

  • [Journal Article] Rhodium-Catalyzed Cross-Coupling of Organoboron Compounds with Vinyl Acetate.2009

    • Author(s)
      Jung-Yi Yu, Ryoichi Kuwano
    • Journal Title

      Angewandte Chemie International Edition Vol.48

      Pages: 7217-7220

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] [4+2] Cycloaddition of o-Xylylenes with Imines Using Palladium Catalyst.2009

    • Author(s)
      Satoshi Ueno, Masakazu Ohtsubo, Ryoichi Kuwano
    • Journal Title

      Journal of the American Chemical Society Vol.131

      Pages: 12904-12905

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Formation of a Carbon-Nitrogen Bond at theβPosition of Saturated Ketones.2009

    • Author(s)
      Satoshi Ueno, Ryosuke Shimizu, Ryoichi Kuwano
    • Journal Title

      Angewandte Chemie International Edition Vol.48

      Pages: 4543-4545

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Transformations of Benzylic Carboxylates and Carbonates.2009

    • Author(s)
      Ryoichi Kuwano
    • Journal Title

      Synthesis

      Pages: 1049-1061

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Formation of a Carbon-Nitrogen Bond at the β Position of Saturated Ketones2009

    • Author(s)
      Satoshi Ueno, et al.
    • Journal Title

      Angewandte Chemie International Edition 48

      Pages: 4543-4545

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] [4+2]Cycloaddition of o-Xylylenes with Imines Using Palladium Catalyst2009

    • Author(s)
      Satoshi Ueno, et al.
    • Journal Title

      Journal of the American Chemical Society 131

      Pages: 12904-12905

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Cross-Coupling of Organoboron Compounds with Vinyl Acetate2009

    • Author(s)
      Jung-Yi Yu, et al.
    • Journal Title

      Angewandte Chemie International Edition 48

      Pages: 7217-7220

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Hydrogenation of 5-Membered Heteroaromatics.2008

    • Author(s)
      Ryoichi Kuwano
    • Journal Title

      Heterocycles Vol.76(総説)

      Pages: 909-922

    • NAID

      40016323197

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Cross-Coupling of Benzylic Carbonates with Organostannanes.2008

    • Author(s)
      Masato Ohsumi, Ryoichi Kuwano
    • Journal Title

      Chemistry Letters Vol.37

      Pages: 796-797

    • NAID

      10021082841

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Benzyl Protection of Phenols under Neutral Conditions: Palladium-Catalyzed Benzylations of Phenols.2008

    • Author(s)
      Ryoichi Kuwano, Hiroki Kusano
    • Journal Title

      Organic Letters Vol.10

      Pages: 1979-1982

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Coupling of Diarylmethyl Carbonates with Arylboronic Acids: A New Access to Triarylmethanes.2008

    • Author(s)
      Jung-Yi Yu, Ryoichi Kuwano, Suzuki Miyaura
    • Journal Title

      Organic Letters Vol.10

      Pages: 973-976

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Hydrogenation of 2, 3, 5-Trisubstituted Pyrroles.2008

    • Author(s)
      Ryoichi Kuwano, Manabu Kashiwabara, Masato Ohsumi, Hiroki Kusano
    • Journal Title

      Journal of the American Chemical Society Vol.130

      Pages: 808-809

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Benzyl Protection of Phenols under Neutral Conditions : Palladium-Catalyzed Benzvlations of Phenols2008

    • Author(s)
      Ryoichi Kuwano, et.al.
    • Journal Title

      Organic Letters 10

      Pages: 1979-1982

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed Cross-coupling of Benzylic Carbonates with Organostannanes2008

    • Author(s)
      Masato Ohsumi, et.al.
    • Journal Title

      Chemistry Letters 37

      Pages: 796-797

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Hydrogenation of 5-Membered Heteroaromatics2008

    • Author(s)
      Ryoichi Kuwano
    • Journal Title

      Heterocycles 76

      Pages: 909-922

    • NAID

      40016323197

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Hydrogenation of 2,3,5-Trisubstituted Pyrroles2008

    • Author(s)
      Ryoichi, Kuwano, et. al.
    • Journal Title

      Journal of the American Chemical Society 130

      Pages: 808-809

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Suzuki-Miyaura Coupling of Diarylmethyl Carbonates with AryIboronic Acids: A New Access to TriaryImethanes.2008

    • Author(s)
      Jung-Yi, Yu, et. al.
    • Journal Title

      Organic Letters 10

      Pages: 973-976

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Coupling of Benzylic Carbonates with Heteroarylboronic Acids.2007

    • Author(s)
      Ryoichi Kuwano, Jung-Yi Yu, Suzuki Miyaura
    • Journal Title

      Heterocycles Vol.74

      Pages: 233-237

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Use of Acetate as a Leaving Group in Palladium- Catalyzed Nucleophilic Substitution of Benzylic Esters.2007

    • Author(s)
      Masashi Yokogi, Ryoichi Kuwnao
    • Journal Title

      Tetrahedron Letters Vol.48

      Pages: 6109-6112

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Formal [4+2] Cycloaddtion of o-Xylylenes with Olefins.2007

    • Author(s)
      Ryoichi, Kuwano, et. al.
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 3802-3803

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] Activation of Carboxylate Functionality with Transition-Metal Catalysis2009

    • Author(s)
      Ryoichi Kuwano
    • Organizer
      The 10th Yeungnam-Kinki Joint Symposium on Organometallic Chemistry
    • Place of Presentation
      Daegu
    • Year and Date
      2009-11-26
    • Related Report
      2009 Annual Research Report
  • [Presentation] Rhodium-Catalyzed Cross-Coupling of Organoborons with Vinyl Acetate2009

    • Author(s)
      Ryoichi Kuwano
    • Organizer
      The 11th International KYOTO conference on New Aspests of Organic Chemistry
    • Place of Presentation
      Kyoto
    • Year and Date
      2009-11-12
    • Related Report
      2009 Annual Research Report
  • [Presentation] 2, 4-二置換ピロールの触媒的不斉水素化2009

    • Author(s)
      三国優太, 桑野良一
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学(船橋市)
    • Year and Date
      2009-03-27
    • Related Report
      2009 Final Research Report
  • [Presentation] 2, 4-二置換ピロールの触媒的不斉水素化2009

    • Author(s)
      三国優太, et.al.
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋市, 日本大学理工学部
    • Year and Date
      2009-03-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] イミダゾールの触媒的不斉水素化2009

    • Author(s)
      篠崎桂一, et.al.
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋市, 日本大学理工学部
    • Year and Date
      2009-03-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] Catalytic Asymmetric Hydrogenation of Aromatic Compounds.2008

    • Author(s)
      Ryoichi Kuwano
    • Organizer
      UK/Japan Joint Symposium on Asymmetric Catalysis (2008)
    • Place of Presentation
      Kyoto University (Kyoto, Japan)
    • Year and Date
      2008-12-08
    • Related Report
      2009 Final Research Report
  • [Presentation] Catalytic Asymmetric Hydrogenation of Aromatic Compounds2008

    • Author(s)
      Ryoichi Kuwano
    • Organizer
      UK/ Japan Joint Symposium on Asymmetric Catalysis (2008)
    • Place of Presentation
      京都市, 京都大学
    • Year and Date
      2008-12-08
    • Related Report
      2008 Annual Research Report
  • [Presentation] ルテニウム触媒を用いたキノリンのベンゼン環選択的な触媒的不斉水素化2008

    • Author(s)
      平佐田一樹, 桑野良一
    • Organizer
      2008年日本化学会西日本大会
    • Place of Presentation
      長崎大学(長崎市)
    • Year and Date
      2008-11-16
    • Related Report
      2009 Final Research Report
  • [Presentation] ルテニウム触媒を用いたナフタレンの触媒的不斉水素化2008

    • Author(s)
      森岡竜一, 柏原学, 桑野良一
    • Organizer
      2008年日本化学会西日本大会
    • Place of Presentation
      長崎大学(長崎市)
    • Year and Date
      2008-11-16
    • Related Report
      2009 Final Research Report
  • [Presentation] ルテニウム触媒を用いたナフタレンの触媒的不斉水素化2008

    • Author(s)
      森岡竜一, et.al.
    • Organizer
      2008年日本化学会西日本大会
    • Place of Presentation
      長崎市, 長崎大学
    • Year and Date
      2008-11-16
    • Related Report
      2008 Annual Research Report
  • [Presentation] ルテニウム触媒を用いたキノリンのベンゼン環選択的な触媒的不斉水素化2008

    • Author(s)
      平佐田一樹, et.al.
    • Organizer
      2008年日本化学会西日本大会
    • Place of Presentation
      長崎市, 長崎大学
    • Year and Date
      2008-11-16
    • Related Report
      2008 Annual Research Report
  • [Presentation] イミダゾールの触媒的不斉水素化2008

    • Author(s)
      篠崎桂一, 桑野良一
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      本大学(船橋市)
    • Year and Date
      2008-03-27
    • Related Report
      2009 Final Research Report
  • [Presentation] Catalytic Asymmetric Hydrogenation of Aromatic Compounds.2007

    • Author(s)
      Ryoichi Kuwano
    • Organizer
      The 3rd PKNU-KU Joint Symposium on Sciences, Progress in Methematics, Physics, and Chemistry
    • Place of Presentation
      Pukyong National University (Pusan, Korea)
    • Year and Date
      2007-11-30
    • Related Report
      2009 Final Research Report
  • [Presentation] Catalytic Asymmetric Hydrogenation of Aromatic Comprunds2007

    • Author(s)
      Ryoichi, Kuwano
    • Organizer
      The 3rd PKNU-KU Joint Symposium on Sciences, Progressin Mathematics, Physics, and Chemistry
    • Place of Presentation
      韓国・釜山・釜慶大学
    • Year and Date
      2007-11-30
    • Related Report
      2007 Annual Research Report
  • [Presentation] Catalytic Asymmetric Hydrogenation of Pyrroles2007

    • Author(s)
      Ryoichi, Kuwano, et. al.
    • Organizer
      14th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      奈良・なら100年会館
    • Year and Date
      2007-08-05
    • Related Report
      2007 Annual Research Report
  • [Book] 使える!有機合成反応241実践ガイド(丸岡啓二, 野崎京子, 石井康敬, 大寺純蔵, 富岡清編)2010

    • Author(s)
      桑野良一
    • Publisher
      化学同人
    • Related Report
      2009 Final Research Report
  • [Book] Chiral Ferrocenes in Asymmetric Catalysis(Li-Xin Dai, Xue-Long Hou, eds.)2010

    • Author(s)
      Ryoichi Kuwano
    • Publisher
      Wiley
    • Related Report
      2009 Final Research Report
  • [Book] Catalysts for Fine Chemical Synthesis, Volume 5, Regio- and Stereo- Controlled Oxidations and Reductions(Stanley M. Roberts, John Whittall, eds.)2007

    • Author(s)
      Ryoichi Kuwano, Masaya Sawamura
    • Publisher
      Wiley
    • Related Report
      2009 Final Research Report
  • [Remarks]

    • URL

      http://www.kyushu-u.ac.jp/pressrelease/2008/2008-03-25.pdf

    • Related Report
      2007 Annual Research Report

URL: 

Published: 2007-04-01   Modified: 2016-04-21  

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