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Creation of Innovative Organocatalysts Utilizing Unique Properties of Unsaturated Medium-size Rings

Research Project

Project/Area Number 16K13994
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

Asano Keisuke  京都大学, 工学研究科, 助教 (90711771)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords有機分子触媒 / 不斉合成 / オレフィン / 中員環 / 面性不斉 / 分子歪み
Outline of Final Research Achievements

The creation of molecular catalysts bearing novel core frameworks offers new systems for organic reactions, and it will advance manufacturing technologies. In this study, we developed organocatalysts utilizing planar chiral medium-size ring structures bearing an olefin and a chiral platform including the olefin, as olefins have hardly been utilized for functional groups for catalysis.
Using trans-cyclooctene catalysts, which were newly synthesized, halogenations of alkenes were investigated; high catalytic activity and large substituent effects, which are important for additional design of the catalysts, were observed. In addition, the hydrophobicity of the hydrocarbon organocatalysts could be applied to phase-transfer catalysis. Furthermore, they were also useful as asymmetric ligands for transition metal catalysts, affording high enantioselectivity.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (40 results)

All 2018 2017 2016 Other

All Journal Article (6 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 6 results,  Acknowledgement Compliant: 3 results,  Open Access: 2 results) Presentation (31 results) (of which Int'l Joint Research: 1 results,  Invited: 3 results) Remarks (3 results)

  • [Journal Article] Induction of Axial Chirality in 8-Arylquinolines via Halogenation Reactions Using Bifunctional Organocatalysts2017

    • Author(s)
      Ryota Miyaji Keisuke Asano Seijiro Matsubara
    • Journal Title

      Chemistry A European Journal

      Volume: 23 Issue: 42 Pages: 9996-10000

    • DOI

      10.1002/chem.201701707

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Bifunctional Organocatalysts for the Asymmetric Synthesis of Axially Chiral Benzamides2017

    • Author(s)
      R. Miyaji, Y. Wada, A. Matsumoto, K. Asano, S. Matsubara
    • Journal Title

      Beilstein J. Org. Chem.

      Volume: 13 Pages: 1518-1523

    • DOI

      10.3762/bjoc.13.151

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Asymmetric Net Cycloaddition for Access to Diverse Substituted 1,5-Benzothiazepines2017

    • Author(s)
      Y. Fukata, K. Yao, R. Miyajio, K. Asano, S. Matsubara
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 23 Pages: 12655-12668

    • DOI

      10.1021/acs.joc.7b02451

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organocatalytic Enantio- and Diastereoselective Cycloetherification via Dynamic Kinetic Resolution of Chiral Cyanohydrins2017

    • Author(s)
      N. Yoneda, Y. Fujii, A. Matsumoto, K. Asano, S. Matsubara
    • Journal Title

      Nat. Chommun.

      Volume: 8 Issue: 1 Pages: 1397-1397

    • DOI

      10.1038/s41467-017-01099-x

    • NAID

      120006364086

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Asymmetric Cycloetherification via the Kinetic Resolution of Alcohols Using Chiral Phosphoric Acid Catalysts2016

    • Author(s)
      Naoki Yoneda, Akira Matsumoto, Keisuke Asano,* and Seijiro Matsubara*
    • Journal Title

      Chemistry Letters

      Volume: 45 Pages: 1300-1303

    • NAID

      130005509389

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 穏和な有機触媒がもたらす精密不斉合成2016

    • Author(s)
      浅野 圭佑*
    • Journal Title

      有機合成化学協会誌

      Volume: 74 Issue: 12 Pages: 1194-1205

    • DOI

      10.5059/yukigoseikyokaishi.74.1194

    • NAID

      130005251191

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] トランスシクロオクテン触媒によるハロラクトン化反応2018

    • Author(s)
      下道 謙太・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 光学活性トランスシクロオクテン配位子によるロジウム触媒不斉1,4-付加反応2018

    • Author(s)
      長野 倫・永成 駿介・下道 謙太・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 二官能性有機触媒を用いた1-(3-hydroxyphenyl)-2-naphthonitrileのハロゲン化による軸不斉構築反応2018

    • Author(s)
      和田 祐希・松本 晃・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 三点不斉一挙構築による光学活性テトラヒドロピラン環形成反応2018

    • Author(s)
      栗本 洋輔・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] Asymmetric Cycloetherification via Cyanation of Acylsilanes Using Bifunctional Organocatalysts2018

    • Author(s)
      Akira Matsumoto, Keisuke Asano, and Seijiro Matsubara
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] インドール誘導体のブロモ環化反応におけるトランスシクロオクテンの添加効果2017

    • Author(s)
      下道 謙太・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス(神奈川県・横浜市)
    • Year and Date
      2017-03-18
    • Related Report
      2016 Research-status Report
  • [Presentation] 2,3-トランス二置換1,5-ベンゾチアゼピンの不斉形式的環化付加合成2017

    • Author(s)
      矢尾 晃一・深田 幸宏・宮地 亮太・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス(神奈川県・横浜市)
    • Year and Date
      2017-03-18
    • Related Report
      2016 Research-status Report
  • [Presentation] Asymmetric Synthesis of 1,3-syn-Diols via Construction of Six-Membered Acetals Using Chiral Phosphoric Acid Catalysts2017

    • Author(s)
      Akira Matsumoto, Keisuke Asano, and Seijiro Matsubara
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス(神奈川県・横浜市)
    • Year and Date
      2017-03-18
    • Related Report
      2016 Research-status Report
  • [Presentation] Development of Novel Bifunctional Bis-base Type Organocatalysts2017

    • Author(s)
      Shunsuke Einaru, Keisuke Asano, and Seijiro Matsubara
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス(神奈川県・横浜市)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] Asymmetric Cycloetherification of 1,3-Diols Using Bifunctional Organocatalysts2017

    • Author(s)
      Yuki Fujii, Keisuke Asano, and Seijiro Matsubara
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] 二官能性有機触媒による対称1,5-ジケトンのエナンチオ選択的環化反応2017

    • Author(s)
      栗本 洋輔・藤井 結稀・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] Construction of Axial Chirality via Selective Halogenation Using Bifunctional Organocatalysts2017

    • Author(s)
      Ryota Miyaji, Keisuke Asano, and Seijiro Matsubara
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] キラルリン酸触媒による六員環アセタール構築を利用した1,3-ジオールの不斉合成2017

    • Author(s)
      松本 晃・浅野 圭佑・松原 誠二郎
    • Organizer
      第111回有機合成シンポジウム2017年【春】
    • Related Report
      2017 Annual Research Report
  • [Presentation] 二官能性有機触媒による対称1,5-ジケトンのエナンチオ選択的環化反応2017

    • Author(s)
      栗本 洋輔・藤井 結稀・浅野 圭佑・松原 誠二郎
    • Organizer
      第111回有機合成シンポジウム2017年【春】
    • Related Report
      2017 Annual Research Report
  • [Presentation] Mild Activations in Organocatalysis for Enantioselective Transformations2017

    • Author(s)
      Keisuke Asano
    • Organizer
      International Symposium on Pure & Applied Chemistry 2017 (ISPAC 2017)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 有機触媒による六員環アセタール構築を利用した1,3-ジオール合成法の開発2017

    • Author(s)
      松本 晃・浅野 圭佑・松原 誠二郎
    • Organizer
      第35回メディシナルケミストリーシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 三点不斉一挙構築を伴う光学活性テトラヒドロピラン環形成2017

    • Author(s)
      栗本 洋輔・藤井 結稀・浅野 圭佑・松原 誠二郎
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] トランスシクロオクテン触媒によるハロラクトン化反応2017

    • Author(s)
      下道 謙太・永成 駿介・浅野 圭佑・松原 誠二郎
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] アノマー効果を利用した動的速度論的分割を伴う不斉シクロエーテル化反応2017

    • Author(s)
      浅野 圭佑・米田 直紀・藤井 結稀・松本 晃・松原 誠二郎
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Organocatalytic Enantio- and Diastereoselective Cycloetherification via Dynamic Kinetic Resolution of Chiral Cyanohydrins2017

    • Author(s)
      Keisuke Asano
    • Organizer
      The 12th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-12)/The 3rd Advanced Research Network on Cutting-Edge Organic Chemistry in Asia (ARNCEOCA-3)
    • Related Report
      2017 Annual Research Report
  • [Presentation] Organocatalytic Enantio- and Diastereoselective Cycloetherification via Dynamic Kinetic Resolution of Chiral Cyanohydrins2017

    • Author(s)
      Keisuke Asano, Naoki Yoneda, Yuki Fujii, Akira Matsumoto, and Seijiro Matsubara
    • Organizer
      The 11th International Symposium on Integrated Synthesis (ISONIS-11)/The 3rd International Symposium on Middle Molecular Strategy (ISMMS-3)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 有機触媒による分子配座の認識に基づく不斉合成2017

    • Author(s)
      浅野 圭佑
    • Organizer
      京都大学理学部 第2回有機若手ワークショップ
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 有機触媒から学ぶ触媒の化学2016

    • Author(s)
      浅野 圭佑
    • Organizer
      第1回ACE meeting @京都
    • Place of Presentation
      京都大学 宇治キャンパス(京都府・宇治市)
    • Year and Date
      2016-11-26
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] キラルリン酸触媒による六員環アセタール構築を利用した1,3-ジオールの不斉合成2016

    • Author(s)
      松本 晃・浅野 圭佑・松原 誠二郎
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都・江戸川区船堀)
    • Year and Date
      2016-11-16
    • Related Report
      2016 Research-status Report
  • [Presentation] 三点不斉一挙構築による含酸素縮環化合物のエナンチオ選択的合成2016

    • Author(s)
      藤井 結稀・浅野 圭佑・松原 誠二郎
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都・江戸川区船堀)
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] キラルリン酸触媒によるアルコールの速度論的分割を伴った不斉環状エーテル化反応2016

    • Author(s)
      浅野 圭佑・米田 直紀・松本 晃・松原 誠二郎
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢歌劇座(石川県・金沢市)
    • Year and Date
      2016-09-26
    • Related Report
      2016 Research-status Report
  • [Presentation] キラルリン酸触媒による六員環アセタール構築を利用した1,3-ジオールの不斉合成2016

    • Author(s)
      松本 晃・浅野 圭佑・松原 誠二郎
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢歌劇座(石川県・金沢市)
    • Year and Date
      2016-09-26
    • Related Report
      2016 Research-status Report
  • [Presentation] 二官能性有機触媒による軸不斉ヘテロビアリールのエナンチオ選択的合成2016

    • Author(s)
      宮地 亮太・浅野 圭佑・松原 誠二郎
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢歌劇座(石川県・金沢市)
    • Year and Date
      2016-09-26
    • Related Report
      2016 Research-status Report
  • [Presentation] キラルリン酸触媒によるアルコールの速度論的分割を伴った不斉環状エーテル化反応2016

    • Author(s)
      浅野 圭佑・米田 直紀・松本 晃・松原 誠二郎
    • Organizer
      第33回有機合成化学セミナー
    • Place of Presentation
      ヒルトンニセコビレッジ(北海道・虻田郡ニセコ町)
    • Year and Date
      2016-09-06
    • Related Report
      2016 Research-status Report
  • [Presentation] キラルリン酸触媒による六員環アセタール構築を利用した1,3-ジオールの不斉合成2016

    • Author(s)
      松本 晃・浅野 圭佑・松原 誠二郎
    • Organizer
      第36回有機合成若手セミナー「明日の有機合成を担う人のために」
    • Place of Presentation
      京都薬科大学 本校地(京都府・京都市)
    • Year and Date
      2016-08-09
    • Related Report
      2016 Research-status Report
  • [Presentation] Asymmetric Synthesis of 1,3-Polyol Building Blocks by Chiral Phosphoric Acid Catalyst2016

    • Author(s)
      Akira Matsumoto, Keisuke Asano, and Seijiro Matsubara
    • Organizer
      The 12th International Symposium on Organic Reactions (ISOR-12)
    • Place of Presentation
      京都テルサ(京都府・京都市)
    • Year and Date
      2016-04-22
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Remarks] 京都大学大学院 工学研究科 材料化学専攻 松原研究室

    • URL

      http://smatsubara.wixsite.com/matsubara-kyoto-u

    • Related Report
      2017 Annual Research Report
  • [Remarks] 有機触媒の化学

    • URL

      http://smatsubara.wixsite.com/matsubara-kyoto-u/organocatalysts-jp

    • Related Report
      2017 Annual Research Report
  • [Remarks] Publications

    • URL

      http://smatsubara.wixsite.com/matsubara-kyoto-u/publications-jp

    • Related Report
      2017 Annual Research Report

URL: 

Published: 2016-04-21   Modified: 2019-03-29  

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