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Development and Application of Supramolecular Asymmetric Catalysts Based on Double-Stranded Helical Structure

Research Project

Project/Area Number 16K17892
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Research InstitutionNagoya University

Principal Investigator

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

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywords超分子 / 二重らせん
Outline of Final Research Achievements

Optically-active double-stranded helices bearing chiral and achiral Co (II) salen complexes and achiral bipyridine N,N'-dioxide in the middle as metal- and organo-catalysts have been designed and synthesized. It was revealed that these one-handed double-helical catalysts remarkably enhanced and/or induced the enantioselectivity in the asymmetric reactions. Moreover, it was found that the [4+4] photocyclodimerization of a carboxylic acid monomer bearing a prochiral 2-substituted anthracene at one end took place regio- (head-to-tail (HT) or head-to-head (HH)), diastereo- (anti or syn), and enantioselectively in the presence of a series of optically-active amidine dimers with a variety of linkers used as templates through complementary amidinium-carboxylate salt bridges.

Report

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

    (22 results)

All 2018 2017 2016

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Open Access: 4 results) Presentation (17 results) (of which Int'l Joint Research: 8 results,  Invited: 2 results)

  • [Journal Article] Chiral Template-Directed Regio-, Diastereo-, and Enantioselective Photodimerization of an Anthracene Derivative Assisted by Complementary Amidinium?Carboxylate Salt Bridge Formation2017

    • Author(s)
      Tanabe, J.; Taura, D.; Ousaka, N.; Yashima, E.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 139 Issue: 21 Pages: 7388-7398

    • DOI

      10.1021/jacs.7b03317

    • NAID

      120006473522

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Thermally Stable Helical Poly(4-carboxyphenyl isocyanide) with a Helicity Memory Assisted by Metal Coordination2017

    • Author(s)
      Daisuke Taura, Naomichi Horimoto, Eiji Yashima
    • Journal Title

      Polymer Journal

      Volume: 49 Issue: 10 Pages: 741-744

    • DOI

      10.1038/pj.2017.41

    • NAID

      120006473523

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Cobalt(II)-Salen-Linked Complementary Double-Stranded Helical Catalysts for Asymmetric Nitro-Aldol Reaction2016

    • Author(s)
      D. Taura, S. Hioki, J. Tanabe, N. Ousaka, E. Yashima
    • Journal Title

      ACS Catal.

      Volume: 6 Issue: 7 Pages: 4685-4689

    • DOI

      10.1021/acscatal.6b01627

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Remarkable Acceleration of Template-Directed Photodimerisation of 9-Phenylethynylanthracene Derivatives Assisted by Complementary Salt Bridge Formation2016

    • Author(s)
      J. Tanabe, D. Taura, N. Ousaka, E. Yashima
    • Journal Title

      Org. Biomol. Chem.

      Volume: 14 Issue: 46 Pages: 10822-10832

    • DOI

      10.1039/c6ob02087a

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions2016

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

      Chem. Rev.

      Volume: 116, Issue: 22 Pages: 13752-13990

    • DOI

      10.1021/acs.chemrev.6b00354

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [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可逆的な構造変換2018

    • Author(s)
      板倉学, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      日本化学会 第98春季年会 (2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] st-PMMAが形成するらせん空孔へのフラーレン誘導体の不斉選択的包接2017

    • Author(s)
      間宮文彦, 見波暁子, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第66回高分子学会年次大会
    • Related Report
      2017 Annual Research 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可逆的な構造変換2017

    • Author(s)
      板倉学, 長坂顕, 服部智成, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第161回東海高分子研究会講演会 (2017年夏期合宿)
    • Related Report
      2017 Annual Research Report
  • [Presentation] アントラセンリンカーを導入したカルボン酸二量体の合成と不斉選択的光二量化反応2017

    • Author(s)
      堀本尚路, 田中真人, 田邉純樹, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第66回高分子討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 2,6-置換アントラセンリンカーを有するカルボン酸二量体の不斉選択的光二量化反応2017

    • Author(s)
      堀本尚路, 田中真人, 田邉純樹, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Enantioselective Encapsulation of Fullerene Derivatives within an Optically-Active Helical st-PMMA Cavity2017

    • Author(s)
      Fumihiko Mamiya, Akiko Minami, Daisuke Taura, Naoki Ousaka, Eiji Yashima
    • Organizer
      The 29th International Symposium on Chirality (Chirality 2017, ISCD-29)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Enantioselective Photodimerization of a Carboxylic Acid Dimer Connected with an Anthracene Linker2017

    • Author(s)
      Naomichi Horimoto, Makoto Tanaka, Junki Tanabe, Daisuke Taura, Naoki Ousaka, Eiji Yashima
    • Organizer
      The 3rd International Symposium on Center of Excellence for Innovative Material Sciences Based on Supramolecules
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Optically-Active Double-Stranded Bipyridine N,N'-Dioxide Helicates and Their Application to Asymmetric Reactions2017

    • Author(s)
      Masayuki Ueda, Taiki Nakamura, Yoshimasa Suzuki, Hiroki Iida, Daisuke Taura, Naoki Ousaka, Eiji Yashima
    • Organizer
      The 7th TOYOTA RIKEN International Workshop on Chirality in Soft Matter
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Enantioselective Photodimerization of a Carboxylic Acid Dimer Linked by a 2,6-Substituted Anthracene Unit2017

    • Author(s)
      Naomichi Horimoto, Makoto Tanaka, Junki Tanabe, Daisuke Taura, Naoki Ousaka, Eiji Yashima
    • Organizer
      The 7th TOYOTA RIKEN International Workshop on Chirality in Soft Matter
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Cobalt(ll)-Salen-Linked Complementary Double Helical Catalysts for Asymmetric Reaction2016

    • Author(s)
      Daisuke Taura, Shogo Hioki, Junki Tanabe, Naoki Ousaka, Eiji Yashima
    • Organizer
      2016 International Symposium on Integrated Molecular/Materials Science and Engineering (IMSE 2016)
    • Place of Presentation
      青島(中国)
    • Year and Date
      2016-10-14
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] An Optically Active Poly(4-isocyanobenzoate) Hydrogel with a Macromolecular Helicity Memory Stabilized by Metal Ion Coordination2016

    • Author(s)
      Naomichi Horimoto, Daisuke Taura, Eiji Yashima
    • Organizer
      2016 International Symposium on Integrated Molecular/Materials Science and Engineering (IMSE 2016)
    • Place of Presentation
      青島(中国)
    • Year and Date
      2016-10-14
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of a Spiroborate-Based Double-Stranded Helicate Bearing Pyrenyl Units and Its Fluorescent Behavior2016

    • Author(s)
      Chiaki Yokota, Yoshimasa Suzuki, Kaori Shimizu, Hiroki Iida, Daisuke Taura, Naoki Ousaka, Eiji Yashima
    • Organizer
      2016 International Symposium on Integrated Molecular/Materials Science and Engineering (IMSE 2016)
    • Place of Presentation
      青島(中国)
    • Year and Date
      2016-10-14
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] キラルなテンプレートを用いたアントラセン誘導体の不斉選択的光二量化反応2016

    • Author(s)
      田邉純樹, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第65回高分子討論会
    • Place of Presentation
      神奈川大学 横浜キャンパス(神奈川県・横浜市)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] 相補的な二重らせん構造を有する有機分子触媒の合成と不斉触媒反応への応用2016

    • Author(s)
      下村昂平, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第65回高分子討論会
    • Place of Presentation
      神奈川大学 横浜キャンパス(神奈川県・横浜市)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] 人工二重らせん分子の合成と応用2016

    • Author(s)
      田浦大輔
    • Organizer
      第86回高分子若手研究会[関西]
    • Place of Presentation
      あうる京北(京都府立ゼミナールハウス)(京都府・京都市)
    • Year and Date
      2016-08-06
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] アントラセンの光二量化を利用した相補鎖のテンプレート合成2016

    • Author(s)
      田邉純樹, 田浦大輔, 逢坂直樹, 八島栄次
    • Organizer
      第65回高分子学会年次大会
    • Place of Presentation
      神戸コンベンションセンター(兵庫県・神戸市)
    • Year and Date
      2016-05-25
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis of Metal-Salen-Linked Complementary Double Helices and Their Application to Asymmetric Catalysis2016

    • Author(s)
      Daisuke Taura, Shogo Hioki, Junki Tanabe, Naoki Ousaka, Eiji Yashima
    • Organizer
      Molecular Chirality Asia 2016
    • Place of Presentation
      大阪(日本)
    • Year and Date
      2016-04-20
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research

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

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