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Development of Optically Active Amine Catalysts with a Propeller-like Chirality for Asymmetric Synthesis

Research Project

Project/Area Number 21550105
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

IRIE Ryo  熊本大学, 大学院・自然科学研究科, 教授 (70243889)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2009: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords有機化学 / 合成化学 / 不斉合成 / 有機触媒 / キラル配位子 / 遷移金属触媒 / 金属中心性不斉 / キラルアミン / 2,6-二置換ピペリジン / キラル四座配位子 / モリブデン錯体 / 不斉エポキシ化 / 2,6-トランス-二置換ピペリジン / 2,6-シス-二置換ピペリジ / 不斉有機触媒 / 金属錯体触媒 / 2,6-トランス-二置換ピベリジン / 2,6-シス-二置換ピベリジ
Research Abstract

New asymmetric cycloisomerization reactions catalyzed by chiral amines have been developed to produce useful optically active furan- and pyran-containing heterobiaryl compounds with axial chirality. Novel chiral carbasugars, which would exhibit unique bioactivities, were also synthesized by using base-catalyzed rearrangement of endoperoxide. Furthermore, unprecedented optically active transition metal complexes with chirality at metal were prepared from a chiral tripodal tetradentate ligand based on tertially amine bearing three different coordination groups.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (33 results)

All 2013 2012 2011 2010 2009 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (22 results) Remarks (5 results)

  • [Journal Article] Synthesis and Stereochemical Behavior of a New Chiral Oxa[7]heterohelicene2011

    • Author(s)
      R. Irie, A. Tanoue, S. Urakawa, T. Imahori, K. Igawa, T. Matsumoto, K. Tomooka, S. Kikuta, T. Uchida, T. Katsuki
    • Journal Title

      Chem. Lett.

      Volume: 40 Pages: 1343-1345

    • NAID

      10030220852

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Convenient Synthesis of meso-Cyclohexa-1,3-dienes by One-Pot Two-Step Deoxygenation of 7-Oxabicyclo-[ 2.2.1]hept-2-enes2011

    • Author(s)
      T. Yano, T. Fujishima, R. Irie
    • Journal Title

      Synthesis

      Pages: 818-822

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Stereochemical Behavior of a New Chiral Oxa[7]heterohelicene2011

    • Author(s)
      Ryo Irie
    • Journal Title

      Chemistry Letters

      Volume: 40 Issue: 12 Pages: 1343-1345

    • DOI

      10.1246/cl.2011.1343

    • NAID

      130004426114

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Diastereoselective Construction of New 5a-Substituted Carbaallose by Exo- β -selective Conjugate Addition to Endo-exo Cross-Conjugated Cyclohexadienone as Key Reaction2010

    • Author(s)
      T. Fujishima, F. Kitoh, T. Yano, R. Irie
    • Journal Title

      Synlett

      Pages: 2279-2282

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Diastereoselective Construction of New 5a-Substituted Carbaallose by exo-β-Selective Conjugate Addition to endo-exo Cross-Conjugated Cyclohexadienone as Key Reaction2010

    • Author(s)
      Takashi Fujishima, Fukashi Kitoh, Tomotsugu Yano, Ryo Irie
    • Journal Title

      Synlett

      Volume: 15 Pages: 2279-2282

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Convenient Synthesis of meso-Cyclohexa-1, 3-dienes by One-Pot Two-Step Deoxygenation of 7-Oxabicyclo[2.2.1]hept-2-enes2010

    • Author(s)
      T.Yano., T.Fujishima, R.Irie
    • Journal Title

      Synthesis 5

      Pages: 818-822

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] o-フェニレンジイン誘導体の環化異性化反応(正宗-Bergman 反応)による非対称ビアリール化合物の合成2013

    • Author(s)
      入江亮, 古澤将樹, 今堀龍志, 井川和宣, 友岡克彦
    • Organizer
      日本化学会第93 春季年会予稿集 3F1-36
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス (大津)
    • Year and Date
      2013-03-24
    • Related Report
      2011 Final Research Report
  • [Presentation] キラルアミン触媒を用いる不斉正宗-Bergman 反応2013

    • Author(s)
      入江亮, 有田光佑, 古澤将樹, 今堀龍志, 井川和宣, 友岡克彦
    • Organizer
      日本化学会第93 春季年会予稿集 3F1-37
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス (大津)
    • Year and Date
      2013-03-24
    • Related Report
      2011 Final Research Report
  • [Presentation] パラジウム触媒を用いるo-フェニレン架橋ビス(アルキニルアレノール)類のタンデム環化芳香族化2012

    • Author(s)
      古澤将樹, 有田光佑, 入江亮,今堀龍志, 井川和宣, 友岡克彦
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都テルサ (京都)
    • Year and Date
      2012-10-12
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthesis, Structure, and Catalytic Properties of Chiral-at-Metal cis-Dioxomolybdenum Complexes2012

    • Author(s)
      増田悠希, 今堀龍志, 森口哲次, 入江亮
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス (大阪), (ポスター賞 (増田))
    • Year and Date
      2012-09-14
    • Related Report
      2011 Final Research Report
  • [Presentation] 金属中心性不斉を有するキラルなシス-ジオキソモリブデン錯体を用いる触媒的不斉エポキシ化の研究2012

    • Author(s)
      増田悠希, 西岡清隆, 今堀龍志, 森口哲次, 入江亮
    • Organizer
      第24回若手研究者のためのセミナー
    • Place of Presentation
      九州大学馬出キャンパス コラボステーションI (福岡)
    • Year and Date
      2012-08-25
    • Related Report
      2011 Final Research Report
  • [Presentation] 金属中心性不斉を有するキラルなシス-ジオキソモリブデン錯体を用いる触媒的不斉エポキシ化の研究2012

    • Author(s)
      増田悠希, 西岡清隆, 今堀龍志, 森口哲次, 入江亮
    • Organizer
      第49回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場 (北九州)
    • Year and Date
      2012-06-30
    • Related Report
      2011 Final Research Report
  • [Presentation] キラルな交差共役シクロヘキサジエノンを鍵中間体とするカルバマンノースの不斉合成2012

    • Author(s)
      坂口洸平, 石川勇人,今堀龍志, 加藤敦 入江亮
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス・矢上キャンパス (横浜)
    • Year and Date
      2012-03-27
    • Related Report
      2011 Final Research Report
  • [Presentation] ピペリジン骨格を基盤とするキラルな三脚型四座配位子の合成とその金属錯体を用いた触媒的不斉酸化反応の開発2011

    • Author(s)
      入江亮
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      崇城大学市民ホール,熊本
    • Year and Date
      2011-10-20
    • Related Report
      2011 Annual Research Report
  • [Presentation] Construction of Oxa-Heterohelicenesby Catalytic Oxidative Tandem Cyclization2011

    • Author(s)
      入江亮
    • Organizer
      第14回アジア化学会議
    • Place of Presentation
      Queen Sirikit National Convention Center, Bangkok, Thailand(招待講演)
    • Year and Date
      2011-09-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] Construction of Catalytic Asymmetric Oxidation Systems with Transition Metal Complexes Coordinated by Piperidine-based Chiral Tripodal Ligands2011

    • Author(s)
      西岡清隆, 今堀龍志, 入江亮
    • Organizer
      第6回日韓天然物化学談話会
    • Place of Presentation
      Seoul National University (Seoul,Korea)
    • Year and Date
      2011-06-24
    • Related Report
      2011 Final Research Report
  • [Presentation] Catalytic Aerobic Oxidative C-C and C-O Coupling Reactions2011

    • Author(s)
      Ryo Irie
    • Organizer
      第6回日韓天然物化学談話会
    • Place of Presentation
      Seoul National University, Seoul, Korea(招待講演)
    • Year and Date
      2011-06-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] Construction of Catalytic Asymmetric Oxidation Systems with Transition Metal Complexes Coordinatedby Piperidine-based Chiral Tripodal Ligands2011

    • Author(s)
      入江亮
    • Organizer
      第6回日韓天然物化学談話会
    • Place of Presentation
      Seoul National University, Seoul, Korea
    • Year and Date
      2011-06-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] キラルな三脚型四座配位子の効率的合成とその金属錯体の不斉触媒機能2010

    • Author(s)
      西岡清隆, 今堀龍志, 入江亮
    • Organizer
      2010年日本化学会西日本大会
    • Place of Presentation
      熊本大学黒髪南キャンパス (熊本)
    • Year and Date
      2010-11-06
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthesis and Characterization of Metal Complexes with Chiral Tripodal Ligand Based on 2,6-cis-Disubstituted Piperidines2010

    • Author(s)
      清田祐基, 濱松真由, 入江亮
    • Organizer
      24th International Conference on Organometallic Chemistry
    • Place of Presentation
      Taipei International Convention Center (台北,China)
    • Year and Date
      2010-07-22
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthesis and Characterizxtion of Metal Complexes with Chiral Tripodal Ligand Based on 2,6-cis-Disubstituted Piperidines2010

    • Author(s)
      清田祐基、濱松真由、入江亮
    • Organizer
      24th International Conference on Organometallic Chemistry
    • Place of Presentation
      台湾・台北市
    • Year and Date
      2010-07-22
    • Related Report
      2010 Annual Research Report
  • [Presentation] 2,6-cis-二置換ピペリジン骨格を基盤とするキラル四座配位子の構築とその金属錯体の触媒機能2010

    • Author(s)
      清田祐基, 濱松真由, 入江亮
    • Organizer
      第47回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場 (北九州)
    • Year and Date
      2010-07-10
    • Related Report
      2011 Final Research Report
  • [Presentation] オキサビシクロ[2.2.1]へプテン誘導体の立体選択的開環反応2010

    • Author(s)
      迎田友里, 入江亮
    • Organizer
      第47回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場 (北九州)
    • Year and Date
      2010-07-10
    • Related Report
      2011 Final Research Report
  • [Presentation] キラルな交差共役シクロヘキサジエノンを鍵中間体とする新規カルバ糖の立体選択的合成2010

    • Author(s)
      竒藤玄, 藤島崇, 矢野友嗣, 入江亮
    • Organizer
      第47回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場 (北九州)
    • Year and Date
      2010-07-10
    • Related Report
      2011 Final Research Report
  • [Presentation] Asymmetric Synthesis of Chiral 2,6-trans-Disubstituted Piperidine Derivatives as Organocatalysts and Ligands2009

    • Author(s)
      濱松真由, 入江亮
    • Organizer
      第11回国際有機化学京都会議 (IKCOC-11)
    • Place of Presentation
      リーガロイヤルホテル (京都)
    • Year and Date
      2009-11-12
    • Related Report
      2011 Final Research Report
  • [Presentation] Asymmetric Synthesis of Chiral 2, 6-trans-Disubstituted Piperidine Derivatives as Organocatalysts and Ligands2009

    • Author(s)
      濱松真由, 入江亮
    • Organizer
      第11回国際有機化学京都会議(IKCOC-11)
    • Place of Presentation
      リーガロイヤルホテル京都
    • Year and Date
      2009-11-12
    • Related Report
      2009 Annual Research Report
  • [Presentation] Synthesis and Reaction of New Endo-exo Cross-conjugated Cyclohexadienone Derivative2009

    • Author(s)
      藤島崇, 矢野友嗣, 中村涼, 竒藤玄, 入江亮
    • Organizer
      第11回国際有機化学京都会議 (IKCOC-11)
    • Place of Presentation
      リーガロイヤルホテル (京都)
    • Year and Date
      2009-11-07
    • Related Report
      2011 Final Research Report
  • [Presentation] 新規交差共役ジエノンの合成とその合成化学的応用2009

    • Author(s)
      入江亮
    • Organizer
      2009年日本化学会西日本大会
    • Place of Presentation
      愛媛大学城北キャンパス (愛媛)
    • Year and Date
      2009-11-06
    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.sci.kumamoto-u.ac.jp/chem/index-j.htm

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.sci.kumamoto-u.ac.jp/~irie/researchactivities/papers.html

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.sci.kumamoto-u.ae.jp/~irie/researchactivities/presentation.html

    • Related Report
      2010 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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