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Direct intra- and intermolecular aldol reactions by catalytic discrimination of aldehydes

Research Project

Project/Area Number 26460007
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionKyoto University

Principal Investigator

Furuta Takumi  京都大学, 化学研究所, 准教授 (30336656)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2015: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2014: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords交差アルドール反応 / 位置選択性 / 立体選択性 / 不斉触媒 / アニリン / 軸性不斉 / 酸塩基触媒 / アニリン型アミノ基 / 位置選択的反応 / 立体選択的反応 / 含窒素複素環
Outline of Final Research Achievements

Catalytic discrimination among similarly reactive functional groups is a key to realizing unique and efficient chemo- and regioselective transformations of multi-functionalized molecules; however, formidable challenges to such discrimination remain.
Upon developing axially chiral aniline-type acid base catlysts, catalytic discrimination among formyl groups bearing similar reactivity was achieved in the highly regio-, diastereo-, and enantioselective intramolecular cross-aldol reactions of enolizable aliphatic dials.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (26 results)

All 2017 2016 2015 2014

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 5 results,  Open Access: 1 results) Presentation (18 results) (of which Int'l Joint Research: 5 results,  Invited: 1 results) Book (1 results)

  • [Journal Article] Asymmetric Intramolecular C-H Insertion Promoted by Dirhodium(II) Carboxylate Catalyst Axially Chiral Amino Acid Derivatives2017

    • Author(s)
      Lu, W.; Pei, X.;Murai, T.; Sasamori, T.; Tlkitoh, N.; Kawabata, T.; Furuta, T.
    • Journal Title

      Synlett,

      Volume: 28 Issue: 06 Pages: 679-683

    • DOI

      10.1055/s-0036-1588674

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Catalytic Discrimination Among Formyl Groups in Regio- and Stereoselective Intramolecular Cross-Aldol Reactions2016

    • Author(s)
      Baba, T.; Yamamoto, J.; Hayashi, K.; Sato, M.; Yamanaka, M.; Kawabata, T.; Furuta, T.
    • Journal Title

      Journal of Chemical Sciences

      Volume: in press Issue: 6 Pages: 3791-3797

    • DOI

      10.1039/c5sc04594k

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Origin of High E-Selectivity in 4-Pyrrolidinopyridine-Catalyzed Tetrasubstituted α,α’-Alkenediol: A Computational and Experimental Study2015

    • Author(s)
      Yamanaka, M.; Yoshida, U.; Sato, M.; Shigeta, T.; Yoshida, K.; Furuta, T.; Kawabata, T.
    • Journal Title

      J. Org. Chem.

      Volume: 80 Issue: 6 Pages: 3075-3082

    • DOI

      10.1021/jo5029453

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Total synthesis of ellagitannins through regioselective sequential functionalization of unprotected glucose2015

    • Author(s)
      H. Takeuchi, K. Mishiro, Y. Ueda, Y. Fujimori, T. Furuta, T. Kawabata
    • Journal Title

      Angewandte Chemie International Edition

      Volume: in press Issue: 21 Pages: 6177-6180

    • DOI

      10.1002/anie.201500700

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Final-stage site-selective acylation for the total syntheses of multifidosides A-C by organocatalysis2015

    • Author(s)
      Ueda, Y.; Furuta, T.; Kawabata, T.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 54 Issue: 41 Pages: 12134-12138

    • DOI

      10.1002/anie.201504729

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Enantioselective Synthesis of SB-2032072014

    • Author(s)
      Yasuo Hirooka, Kazutada Ikeuchi, Yuichiro Kawamoto, Yusuke Akao, Takumi Furuta, Tomohiro Asakawa, Makoto Inai, Toshiyuki Wakimoto, Tohru Fukuyama and Toshiyuki Kan
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 6 Pages: 1646-1646

    • DOI

      10.1021/ol5002973

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Oxidative kinetic resolution of racemic alkyl aryl carbinols by an electronically tuned chiral nitroxyl radical2014

    • Author(s)
      Hamada, S.; Wada, Y.; Sasamori, T.; Tokitoh, N.; Furuta, T.; Kawabata, T.
    • Journal Title

      Tetrahedron Lett

      Volume: 55 Issue: 11 Pages: 1943-1945

    • DOI

      10.1016/j.tetlet.2014.02.005

    • NAID

      120005439590

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] アニリン型触媒による脂肪族アルデヒドの分子間不斉交差 アルドール反応2017

    • Author(s)
      新宮るり、田中雄也、馬場智明、古田 巧、川端猛夫
    • Organizer
      日本薬学会第 137 年会
    • Place of Presentation
      東北大学薬学部(宮城・仙台)
    • Related Report
      2016 Annual Research Report
  • [Presentation] 分子内不斉C-H挿入反応によるα-アリール-β-置換-γ-ラクトンの立体選択的合成2017

    • Author(s)
      陸 文傑、Pei Xu、○村井琢哉、笹森貴裕、時任宣博、川端猛夫、古田 巧
    • Organizer
      日本薬学会第 137 年会
    • Place of Presentation
      東北大学薬学部(宮城・仙台)
    • Related Report
      2016 Annual Research Report
  • [Presentation] 触媒制御による脂肪族アルデヒドの直接的分子間不斉交差アルドール反応2016

    • Author(s)
      新宮るり、田中雄也、馬場智明、古田 巧、川端猛夫
    • Organizer
      第 66 回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪薬科大学(大阪・高槻)
    • Related Report
      2016 Annual Research Report
  • [Presentation] 水素結合に基づくロジウム触媒分子内不斉C-H 挿入反応2016

    • Author(s)
      陸 文傑、ジョ ハイ、笹森貴裕、時任宣博、古田 巧、川端猛夫
    • Organizer
      第 63 回有機金属化学討論会
    • Place of Presentation
      早稲田大学西早稲田キャンパス(東京・新宿)
    • Related Report
      2016 Annual Research Report
  • [Presentation] アニリン型酸塩基触媒による脂肪族アルデヒドの直接的分子間不斉交差アルドール反応2016

    • Author(s)
      新宮るり、田中雄也、馬場智明、古田 巧、川端猛夫
    • Organizer
      日本プロセス化学会 2016 サマーシンポジウム
    • Place of Presentation
      名古屋国際会議場(愛知。名古屋)
    • Related Report
      2016 Annual Research Report
  • [Presentation] Catalytic discrimination of formyl groups: Regio- and stereoselective intramolecular cross-aldol reaction of enolizable aliphatic dials promoted by aniline-type acid base catalyst2016

    • Author(s)
      Takumi Furuta, Tomonori Baba, Ramesh Yella, Yuya Tanaka, Satoru Yamamoto, Takeo Kawabata
    • Organizer
      17th Tetrahedron Symposium
    • Place of Presentation
      Sitges (Spain)
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 分子認識型ロジウム触媒による分子内不斉 C-H 挿入反応2016

    • Author(s)
      陸 文傑、徐ハイ、笹森貴裕、時任宣博、古田 巧、川端猛夫
    • Organizer
      第 11 回有機元素セミナー
    • Place of Presentation
      京都大学宇治キャンパス(京都・宇治)
    • Related Report
      2016 Annual Research Report
  • [Presentation] Hydrogen-Bond Mediated Enantioselectivity in a C-H Insertion Reaction Promoted by Rh Carboxylate Catalyst2016

    • Author(s)
      Wen-jie Lu, Pei Xu, Takumi Furuta, Takeo Kawabata
    • Organizer
      Molecular Chirality Asia 2016
    • Place of Presentation
      Osaka (Japan)
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Stereoselective Intermolecular Cross-Aldol Reaction of Aliphatic Aldehydes Promoted by Aniline-Type Acid Base Catalyts2016

    • Author(s)
      Yuya Tanaka, Ruri Shimmiya, Tomonori Baba, Takumi Furuta, Takeo Kawabata
    • Organizer
      Molecular Chirality Asia 2016
    • Place of Presentation
      Osaka (Japan)
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ホルミル基の触媒的識別:アニリン型酸-塩基触媒による脂肪族ジアールの分子内不斉交差アルドール反応2015

    • Author(s)
      古田 巧、馬場智明、Ramesh Yella、田中雄也、山本 覚、山本純也、佐藤 真、山中正浩、川端猛夫
    • Organizer
      第41回 反応と合成の進歩シンポジウム
    • Place of Presentation
      近畿大学11月ホール(大阪府・東大阪市)
    • Year and Date
      2015-10-27
    • Related Report
      2015 Research-status Report
  • [Presentation] Stereoselective Intramolecular Cross-aldol and Desymmetrization of Aliphatic Dials Enabled by Axially Chiral Aniline-type Catalyst2015

    • Author(s)
      Tomonori Baba, Ramesh Yella, Yuya Tanaka, Satoru Yamamoto, Takumi Furuta, and Takeo Kawabata
    • Organizer
      The 3rd International Symposium on Process Chemistry
    • Place of Presentation
      Kyoto International Conference Center(京都府・京都市)
    • Year and Date
      2015-07-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Catalytic Discrimination of Formyl Groups: Regio- and Stereoselective Intramolecular Cross-Aldol Reaction of Enolizable Dials Promoted by Amine Catalyst with Low Reactivity2015

    • Author(s)
      Takumi Furuta, Tomonori Baba, Ramesh Yella, Yuya Tanaka, Satoru Yamamoto, and Takeo Kawabata
    • Organizer
      The 39th Naito Conference: The chemstry of organocatalysts
    • Place of Presentation
      CATREAISE Gateaux Kingdom SAPPORO(北海道・札幌市)
    • Year and Date
      2015-07-07
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] ビアリール型アミノ酸を起点とする分子認識型触媒の開発2014

    • Author(s)
      古田 巧
    • Organizer
      第12回有機合成化学協会関西支部賞受賞講演会
    • Place of Presentation
      大阪科学技術センター(大阪)
    • Year and Date
      2014-12-02
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] 軸性不斉アニリン型酸―塩基触媒による分子内不斉交差アルドール反応2014

    • Author(s)
      馬場 智明,山本 純也,古田 巧,川端 猛夫
    • Organizer
      第105回有機合成シンポジウム2014年(秋)
    • Place of Presentation
      東京、タワーホール船堀
    • Year and Date
      2014-11-06
    • Related Report
      2014 Research-status Report
  • [Presentation] アニリン型酸―塩基触媒による分子内不斉交差アルドール反応2014

    • Author(s)
      馬場 智明,山本 純也,古田 巧,川端 猛夫
    • Organizer
      第64回 日本薬学会近畿支部総会・大会
    • Place of Presentation
      京都薬科大学(京都)
    • Year and Date
      2014-10-11
    • Related Report
      2014 Research-status Report
  • [Presentation] アニリンアミノ基を活性中心とした酸―塩基触媒による分子内不斉交差アルドール反応2014

    • Author(s)
      馬場 智明,山本 純也,古田 巧,川端 猛夫
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      札幌市民ホール(札幌)
    • Year and Date
      2014-09-11
    • Related Report
      2014 Research-status Report
  • [Presentation] 軸性不斉アニリン触媒による分子内不斉交差アルドール反応2014

    • Author(s)
      馬場 智明,山本 純也,古田 巧,川端 猛夫
    • Organizer
      「有機分子触媒による未来型分子変換」 第4回公開シンポジウム  分子活性化―有機分子触媒合同シンポジウム
    • Place of Presentation
      北海道大学学術交流会館(札幌)
    • Year and Date
      2014-06-20
    • Related Report
      2014 Research-status Report
  • [Presentation] 軸性不斉アニリン型酸―塩基触媒による分子内不斉交差アルドール反応2014

    • Author(s)
      馬場 智明,山本 純也,古田 巧,川端 猛夫
    • Organizer
      シンポジウム モレキュラー・キラリティー2014
    • Place of Presentation
      仙台国際センター(仙台)
    • Year and Date
      2014-06-07
    • Related Report
      2014 Research-status Report
  • [Book] RSC Green Chemistry, Sustainable Catalysis, Chiral Imidazole and Pyridines as Asymmetric Organocatalysis2016

    • Author(s)
      Furuta, T.; Kawabata, T.
    • Total Pages
      30
    • Publisher
      The Royal Society of Chemistry
    • Related Report
      2016 Annual Research Report

URL: 

Published: 2014-04-04   Modified: 2018-03-22  

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