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Synthesis of optically active N-C axially chiral amines through enantioselective isomerization

Research Project

Project/Area Number 26460014
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionShibaura Institute of Technology

Principal Investigator

kitagawa osamu  芝浦工業大学, 工学部, 教授 (30214787)

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: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords軸不斉 / アミン / 回転障壁 / プロトン酸 / エナンチオマー / 異性化 / エナンチマー / エナンチオ選択性 / エナンチオ選択的 / ルイス酸
Outline of Final Research Achievements

We succeeded in the synthesis of optically active N-C axially chiral amines and found their notable structural property. The addition of protic acid to N-C axially chiral cyclic amine brought about significant increase in the rotation rate around the chiral axis due to the formation of the protonated amine (Proton accelerator). On the other hand, N-C axially chiral amines, which result in the decrease in the rotation rate around the chiral axis by the addition of protic acid, was also found (Proton brake). Furthermore, we elucidated the mechanism of Proton accelerator and Proton brake through X-ray crystal structural analysis and DFT calculation.

Report

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

    (9 results)

All 2016 2015

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 3 results,  Open Access: 2 results) Presentation (6 results)

  • [Journal Article] Enantioselective synthesis of N-C axially chiral indoles through chiral palladium-catalyzed 5-endo-hydroaminocyclization2016

    • Author(s)
      Yudai Morimoto, Satoshi Shimizu, Ayano Mokuya, Nobutaka Ototake, Osamu Kitagawa
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 34 Pages: 5221-5229

    • DOI

      10.1016/j.tet.2015.05.001

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] The Syntesisi of optically active N-C axially chiral tetrahydroquinoline and its response to an acid-accelerated molecular rotor2015

    • Author(s)
      Yuya Suzuki, Masato, Kageyama, Ryuichi Morisawa, Yasuo Dobashi, Hiroshi Hasegawa, Satoshi Yokojima, Osamu Kitagawa
    • Journal Title

      Chemical Communications

      Volume: 51 Issue: 56 Pages: 11229-11232

    • DOI

      10.1039/c5cc03659c

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobezoquinolin-2-one2015

    • Author(s)
      Yuya Suzuki, Isao Takahashi, Yasuo Dobashi, Hiroshi Hasegawa, Christian Roussel, Osamu Kitagawa
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 1 Pages: 132-135

    • DOI

      10.1016/j.tetlet.2014.11.040

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] 新規炭素-窒素軸不斉アミンの創製と構造特性2016

    • Author(s)
      森澤龍一,岩﨑由美子,北川 理
    • Organizer
      第72回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟薬科大学新津東キャンパス
    • Year and Date
      2016-11-26
    • Related Report
      2016 Annual Research Report
  • [Presentation] 新規な炭素-窒素軸不斉アミンの合成と構造特性2016

    • Author(s)
      森澤龍一,岩﨑由美子,北川 理
    • Organizer
      第60回日本薬学会関東支部大会
    • Place of Presentation
      東京大学
    • Year and Date
      2016-09-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] 炭素-窒素軸不斉アミンの創製と構造特性2016

    • Author(s)
      森澤龍一、大林竜太、滝本裕也、北川理
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜
    • Year and Date
      2016-03-28
    • Related Report
      2015 Research-status Report
  • [Presentation] 炭素-窒素軸不斉ベンゾキノリノン誘導体の特異な立体構造と回転障壁2015

    • Author(s)
      鈴木裕哉,高橋 功,長谷川弘,北川 理
    • Organizer
      第58回日本薬学会関東支部大会
    • Place of Presentation
      昭和薬科大学(町田市)
    • Year and Date
      2015-10-04
    • Related Report
      2014 Research-status Report
  • [Presentation] 炭素-窒素軸不斉環状アミンを利用したプロトングリース分子:不斉軸回転機構の考察2015

    • Author(s)
      森澤龍一,鈴木裕哉,北川 理,長谷川弘,横島 智
    • Organizer
      モレキュラーキラリティー2015
    • Place of Presentation
      東京(早稲田大学)
    • Year and Date
      2015-06-12
    • Related Report
      2015 Research-status Report
  • [Presentation] 炭素-窒素軸不斉テトラヒドロキノリノンの触媒的不斉合成とプロトングリース分子への応用2015

    • Author(s)
      鈴木裕哉,景山允人,北川 理
    • Organizer
      第67回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      慶応義塾大学理工学部矢上キャンパス
    • Year and Date
      2015-05-17
    • Related Report
      2014 Research-status Report

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

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