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Development of Highly Effective and Selective Supramolecular Asymmetric Catalysts Based on Double-Helical Framework

Research Project

Project/Area Number 18K05059
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 32020:Functional solid state chemistry-related
Research InstitutionNagoya University

Principal Investigator

Taura Daisuke  名古屋大学, 工学研究科, 助教 (20622450)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords超分子 / 二重らせん
Outline of Final Research Achievements

In this work, an optically-active complementary double helix bearing the achiral bifunctional organocatalyst unit was first found to catalyze the asymmetric direct aldol reaction of cyclohexanone with 4-nitrobenzaldehyde. Moreover, the photoirradiation of the anthracene derivative introduced in the middle of the one-handed double-helical framework induced by chiral amines proceeded in a highly enantiodifferentiating manner to afford the chiral anti-photodimer with up to 98% enantiomeric excess (ee).

Academic Significance and Societal Importance of the Research Achievements

DNAのらせんキラリティを巧みに活用したハイブリッド不斉触媒の報告例はあるものの、人工二重らせんを基盤とする超分子不斉触媒や二重らせんのキラル空間に由来する不斉反応の開発に関する研究例は、研究代表者の報告以外にはほとんどない。すなわち、本研究成果は、キラルならせんが創出する空間が不斉選択性の発現に極めて重要であることを実証するだけではなく、既存の方法では実現が困難な不斉反応の開拓にも繋がり、その学術的・社会的意義は極めて大きい。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (28 results)

All 2021 2020 2019 2018 Other

All Journal Article (9 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 9 results,  Open Access: 3 results) Presentation (17 results) (of which Int'l Joint Research: 5 results) Remarks (2 results)

  • [Journal Article] Water-Mediated Reversible Control of Three-State Double-Stranded Titanium(IV) Helicates2021

    • Author(s)
      N. Ousaka, M. Itakura, A. Nagasaka, M. Ito, T. Hattori, D. Taura, T. Ikai, E. Yashima
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 143 Issue: 11 Pages: 4346-4358

    • DOI

      10.1021/jacs.0c13351

    • NAID

      120007169528

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Formation of Spiroborate-Based Double-Stranded hetero-Helicates Assisted by Donor-Acceptor Interactions2021

    • Author(s)
      D. Taura, X. Wang, M. Ito, E. Yashima
    • Journal Title

      Org. Chem. Front.

      Volume: 8 Issue: 11 Pages: 2551-2555

    • DOI

      10.1039/d1qo00286d

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Chiral Guest-Induced Catalytic Deracemization of a Spiroborate-Based Double-Stranded Helicate Bearing a Bisporphyrin Unit with Acids2020

    • Author(s)
      M. Ito, T. Ikai, S. Yamamoto, D. Taura, N. Ousaka, E. Yashima
    • Journal Title

      Chem. Lett.

      Volume: 49 Issue: 9 Pages: 1030-1033

    • DOI

      10.1246/cl.200352

    • NAID

      130007897102

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Remote-Controlled Regio- and Diastereodifferentiating Photodimerization of a Dynamic Helical Peptide-Bound 2-Substituted Anthracene2020

    • Author(s)
      D. Taura, A. Urushima, Y. Sugioka, N. Ousaka, E. Yashima
    • Journal Title

      Chem. Commun.

      Volume: 56 Issue: 87 Pages: 13433-13436

    • DOI

      10.1039/d0cc06164f

    • NAID

      120007146024

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Helix-Sense-Selective Encapsulation of Helical Poly(lactic acid)s within a Helical Cavity of Syndiotactic Poly(methyl methacrylate) with Helicity Memory2020

    • Author(s)
      Tomoyuki Ikai, Satoshi Kawabata, Fumihiko Mamiya, Daisuke Taura, Naoki Ousaka, and Eiji Yashima
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 52 Pages: 21913-21925

    • DOI

      10.1021/jacs.0c11204

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Complementary Double-Stranded Helical Oligomers Bearing Achiral Bifunctional Groups That Catalyze Asymmetric Aldol Reaction2020

    • Author(s)
      D. Taura, K. Shimomura, N. Ousaka, E. Yashima
    • Journal Title

      Chirality

      Volume: 32 Issue: 3 Pages: 254-264

    • DOI

      10.1002/chir.23169

    • NAID

      120006848993

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Enantiodifferentiating Photodimerization of a 2,6-Disubstituted Anthracene Assisted by Supramolecular Double-Helix Formation with Chiral Amines2020

    • Author(s)
      A. Urushima, D. Taura, M. Tanaka, N. Horimoto, J. Tanabe, N. Ousaka, T. Mori, E. Yashima
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 59 Issue: 19 Pages: 7478-7486

    • DOI

      10.1002/anie.201916103

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Fluorescent Molecular Spring That Visualizes the Extension and Contraction Motions of a Double-Stranded Helicate Bearing Terminal Pyrene Units Triggered by Release and Binding of Alkali Metal Ions2019

    • Author(s)
      D. Taura, K. Shimizu, C. Yokota, R. Ikeda, Y. Suzuki, H. Iida, N. Ousaka, E. Yashima
    • Journal Title

      Chem. Commun.

      Volume: 55 Issue: 80 Pages: 12084-12087

    • DOI

      10.1039/c9cc06126f

    • NAID

      120006786252

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Spiroborate-Based Double-Stranded Helicates: Meso-to-Racemo Isomerization and Ion-Triggered Springlike Motion of the Racemo-Helicate2018

    • Author(s)
      N. Ousaka, K. Shimizu, Y. Suzuki, T. Iwata, M. Itakura, D. Taura, H. Iida, Y. Furusho, T. Mori, E. Yashima
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 140 Issue: 25 Pages: 17027-17039

    • DOI

      10.1021/jacs.8b02388

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] 異種の分子鎖からなる二重らせんホウ素ヘリケートの選択的形成2020

    • Author(s)
      田浦大輔, 王翔, 伊藤正樹, 八島栄次
    • Organizer
      第69回高分子学会年次大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ドナー-アクセプター相互作用を駆動力とした二重らせんホウ素ヘテロヘリケートの選択的形成2020

    • Author(s)
      田浦大輔, 王翔, 伊藤正樹, 八島栄次
    • Organizer
      第69回高分子討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] キラルゲストを包接したビスポルフィリン部位を有する二重らせんホウ素ヘリケートのブレンステッド酸を用いた触媒的デラセミ化反応2020

    • Author(s)
      伊藤正樹, 田浦大輔, 逢坂直樹, 井改知幸, 八島栄次
    • Organizer
      第69回高分子討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] st-PMMAのらせん空孔を用いたフラーレン含有ポリラクチドの不斉選択的包接2020

    • Author(s)
      川端賢, 間宮文彦, 田浦大輔, 逢坂直樹, 井改知幸, 八島栄次
    • Organizer
      第69回高分子討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Acid-Promoted Deracemization of a Spiroborate-Based Double-Stranded Helicate Bearing a Bisporphyrin Unit through Inclusion Complexation with Chiral Guests2020

    • Author(s)
      M. Ito, D. Taura, N. Ousaka, T. Ikai, E. Yashima
    • Organizer
      The Molecular Chirality Asia 2020
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Helix-Sense-Selective Encapsulation of Fullerene-Bound Polylactides within the Helical Cavity of st-PMMA with a Helicity Memory2020

    • Author(s)
      S. Kawabata, F. Mamiya, D. Taura, N. Ousaka, T. Ikai, E. Yashima
    • Organizer
      The Molecular Chirality Asia 2020
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Spiroborate-Based Homo and Hetero Double-Strand Helicates2019

    • Author(s)
      X. Wang, M. Ito, A. Urushima, D. Taura, E. Yashima
    • Organizer
      The 31st International Symposium on Chirality (Chirality 2019, ISCD-31)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Acid-Promoted Deracemization of a Spiroborate-Based Double-Stranded Helicate Bearing a Bisporphyrin Unit through Inclusion Complexation with Chiral Guests2019

    • Author(s)
      M. Ito, X. Wang, S. Yamamoto, D. Taura, N. Ousaka, T. Ikai, E. Yashima
    • Organizer
      2nd G'L'owing Polymer Symposium in KANTO (GPS-K 2019)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 2,6位置換アントラセンリンカーを有するカルボン酸二量体へのキラルアミンによる一方向巻き二重らせん誘起とその不斉選択的光二量化反応2019

    • Author(s)
      宇留嶋彬央, 田浦大輔, 堀本尚路, 田邉純樹, 逢坂直樹, 森直, 八島栄次
    • Organizer
      シンポジウム モレキュラー・キラリティー2019 (MC2019)
    • Related Report
      2019 Research-status Report
  • [Presentation] st-PMMAのキラルならせん空孔へのペプチドおよびポリラクチドを有するフラーレン誘導体の不斉選択的包接2019

    • Author(s)
      川端賢, 間宮文彦, 林矩生, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第68回高分子討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] 光学活性ゲストを包接したビスポルフィリン部位を有する二重らせんホウ素ヘリケートの酸による効率的デラセミ化反応2019

    • Author(s)
      伊藤正樹, 山本慎也, Xiang Wang, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第9回CSJ化学フェスタ
    • Related Report
      2019 Research-status Report
  • [Presentation] 光学活性ゲストを包接したビスポルフィリン部位を有する二重らせんホウ素ヘリケートの酸によるデラセミ化反応2019

    • Author(s)
      伊藤正樹, 山本慎也, Xiang Wang, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第50回中部化学関係学協会支部連合秋季大会
    • Related Report
      2019 Research-status Report
  • [Presentation] st-PMMAの形成するキラルなラセン空孔を利用したフラーレン誘導体のエナンチオ選択的な包接錯体形成と光学分割への応用2019

    • Author(s)
      田浦大輔, 間宮文彦, 川端賢, 林矩生, 見波暁子, 逢坂直樹, 八島栄次
    • Organizer
      第28回ポリマー材料フォーラム
    • Related Report
      2019 Research-status Report
  • [Presentation] Enantioselective Photodimerization of a 2,6-Disubstituted Anthracene Derivative Assisted by a One-Handed Homo-Double Helix Formation2019

    • Author(s)
      A. Urushima, M. Tanaka, N. Horimoto, J. Tanabe, D. Taura, N. Ousaka, T. Mori, E. Yashima
    • Organizer
      日本化学会 第99春季年会 (2019)
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis of a Double-Stranded Titanium(IV) Helicate Composed of Oligophenol Units and Its Reversible Meso-Racemo Conversion2018

    • Author(s)
      M. Itakura, A. Nagasaka, D. Taura, N. Ousaka, E. Yashima
    • Organizer
      The 30th International Symposium on Chirality (Chirality 2018, ISCD-30)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] オリゴフェノール誘導体からなる二重らせんチタンヘリケートの合成とその動的メソ-ラセモ変換2018

    • Author(s)
      板倉学, 長坂顕, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      シンポジウム モレキュラー・キラリティー2018 (MC2018)
    • Related Report
      2018 Research-status Report
  • [Presentation] オリゴフェノール誘導体からなる二重らせんチタンヘリケートの合成とその動的構造変換2018

    • Author(s)
      板倉学, 長坂顕, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第67回高分子学会年次大会
    • Related Report
      2018 Research-status Report
  • [Remarks] 名古屋大学大学院工学研究科有機・高分子化学専攻八島研究室

    • URL

      http://www.helix.chembio.nagoya-u.ac.jp/j/TOP.html

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
  • [Remarks] 名古屋大学大学院工学研究科有機・高分子化学専攻八島研究室

    • URL

      http://www.helix.chembio.nagoya-u.ac.jp/

    • Related Report
      2018 Research-status Report

URL: 

Published: 2018-04-23   Modified: 2022-01-27  

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