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Design of novel chirality of macrocyclic compound bearing heteroaromatic biaryls

Research Project

Project/Area Number 24655083
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKobe University

Principal Investigator

MORI Atsunori  神戸大学, 工学(系)研究科(研究院), 教授 (90210111)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2012: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords分子不斉 / ヘテロ芳香族 / キラルHPLC / CHホモカップリング / 閉環メタセシス / イミダゾール / チオフェン / X線結晶構造解析 / ヘテロビアリール / 軸性不斉 / ルテニウム触媒 / 光学分割 / ビスアゾール
Research Abstract

Design of winding-vine-shaped organic molecule was carried out. The obtained compound was found to show molecular asymmetry, which is a molecule with no carbogenic chiral center. Imidazole derivatives as a nitrogen-containing heteroaromatic compound was subjected to CH homocoupling reaction and following ruthenium-catalyzed ring-closing metathesis leading to the compounds showing molecular asymmetry. The structure of the obtained molecule was confirmed by X-ray structure analysis and its chirality was revealed by HPLC analysis with a chiral column. Separation of both enantiomers were also achievled by the resolution with a preparative chiral column. The related compound of molecular asymmetry was also prepared with a thiophene derivative, which was a heteroaromatic compound bearing a sulfur atom.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (21 results)

All 2014 2013 2012 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (11 results) (of which Invited: 4 results) Remarks (2 results)

  • [Journal Article] Synthesis and properties of regioregular poly(3-substituted thiophene) bearing disiloxane moiety in the substituent. Remarkably high solubility in hexane2014

    • Author(s)
      Atsunori Mori, Kenji Ide, Shunsuke Tamba, Satoru Tsuji, Yuka Toyomori, Takeshi Yasuda
    • Journal Title

      Chemistry Letters

      Volume: 41巻(印刷中)

    • NAID

      130004868129

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and properties of regioregular poly (3-substituted thiophene) bearing disiloxane moiety in the substituent. Remarkably high solubility in hexane.2014

    • Author(s)
      Atsunori Mori, Kenji Ide, Shunsuke Tamba, Satoru Tsuji, Yuka Toyomori, Takeshi Yasuda.
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 5 Pages: 640-642

    • DOI

      10.1246/cl.131222

    • NAID

      130004868129

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Studies on the preference of multiple coupling in the introduction of thiophene ring into poly-halogenated aromatic compounds with nickel NHC catalyst2013

    • Author(s)
      Shota Tanaka, Go Tatsuta, Atsushi Sugie, Atsunori Mori
    • Journal Title

      Tetrahedron Letters

      Volume: 54巻 Pages: 1976-1979

    • NAID

      120006220754

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Studies on the preference of multiple coupling in the introduction of thiophene ring into poly-halogenated aromatic compounds with nickel NHC catalyst2013

    • Author(s)
      Shota Tanaka
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 15 Pages: 1976-1979

    • DOI

      10.1016/j.tetlet.2013.01.127

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-catalyzed oxidative C?H, N?H coupling of azoles and thiophenes2012

    • Author(s)
      Shinobu Mitsuda, Taiki Fujiwara, Katsuyoshi Kimigafukuro, Daiki Monguchi, Atsunori Mori
    • Journal Title

      Tetrahedron

      Volume: 68巻 Pages: 3585-3595

    • NAID

      120006220751

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Axially chiral macrocyclic E-alkene bearing bisazole component formed by sequential C?H homocoupling and ring-closing metathesis2012

    • Author(s)
      Shotaro Nishio, Takashi Somete, Atsushi Sugie, Tohru Kobayashi, Tsuyoshi Yaita, Atsunori Mori
    • Journal Title

      Organic Letters

      Volume: 14巻 Pages: 2476-2479

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Axially chiral macrocyclic E-alkene bearing bisazole component formed by sequential C‒H homocoupling and ring-closing metathesis2012

    • Author(s)
      Shotaro Nishio
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 10 Pages: 2476-2479

    • DOI

      10.1021/ol300755y

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-catalyzed oxidative C-H, N-H coupling of azoles and thiophenes2012

    • Author(s)
      Shinobu Mitsuda
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 18 Pages: 3585-3595

    • DOI

      10.1016/j.tet.2012.03.001

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] ヘテロ芳香族化合物のCHカップリング反応新反応開発から応用まで2013

    • Author(s)
      森敦紀
    • Organizer
      神戸薬科大学学術講演会
    • Place of Presentation
      神戸薬科大学
    • Year and Date
      2013-12-19
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] 軸性不斉イミダゾール骨格を有する大環状化合物の合成2013

    • Author(s)
      岡山陽一,辻悟,西尾正太郎,染手隆志,杉江敦司,小林徹,矢板毅,森敦紀
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Year and Date
      2013-09-06
    • Related Report
      2013 Final Research Report
  • [Presentation] 軸性不斉ビチオフェン骨格を有する大環状化合物の合成2013

    • Author(s)
      辻悟,光田紫乃布,岡山陽一,杉江敦司,小林徹,宮崎有史,矢板毅,森敦紀
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Year and Date
      2013-09-06
    • Related Report
      2013 Final Research Report
  • [Presentation] ビチオフェン骨格をもつ大環状アルケンのE選択的合成2013

    • Author(s)
      辻悟,光田紫乃布,岡山陽一,杉江敦司,森敦紀
    • Organizer
      第33回有機合成若手セミナー
    • Place of Presentation
      神戸大学
    • Year and Date
      2013-08-02
    • Related Report
      2013 Final Research Report
  • [Presentation] C-H coupling reactions of heteroaromatic compounds by transition-matal catalysis2013

    • Author(s)
      Atsunori Mori
    • Organizer
      4th International conference for Young Chemists
    • Place of Presentation
      マレーシア
    • Year and Date
      2013-02-01
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] ヘテロ芳香族化合物の触媒的カップリング 新反応開発から応用まで2013

    • Author(s)
      森 敦紀
    • Organizer
      神戸薬科大学学術講演会
    • Place of Presentation
      神戸薬科大学
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 軸性不斉ビチオフェン骨格を有する大環状化合物の合成2013

    • Author(s)
      辻 悟・光田紫乃布・岡山陽一・杉江敦司・小林 徹・矢板 毅・宮崎有史・森 敦紀
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 軸性不斉ビスイミダゾール骨格を有する大環状化合物の合成2013

    • Author(s)
      岡山 陽一・辻 悟・西尾 正太郎・染手 隆志・杉江 敦司・小林 徹・矢板 毅,森 敦紀
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] ビチオフェン骨格をもつ大環状アルケンのE選択的合成2013

    • Author(s)
      辻 悟,光田紫乃布,岡山陽一,杉江敦司,森 敦紀
    • Organizer
      第33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
      神戸大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] C-H coupling reactions of heteroaromatic compounds by transition-matal catalysis2013

    • Author(s)
      Atsunori Mori
    • Organizer
      4th International conference for Young Chemists
    • Place of Presentation
      Penang, Malaysia
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] ビスアゾール誘導体の閉環メタセシスによるE型大環状アルケンの合成と軸性不斉の発現2012

    • Author(s)
      辻悟,森敦紀
    • Organizer
      第39回有機反応懇談会
    • Place of Presentation
      関西大学
    • Year and Date
      2012-08-03
    • Related Report
      2013 Final Research Report 2012 Research-status Report
  • [Remarks]

    • URL

      http://seesaawiki.jp/w/moriorg3/d/Topics?wiki_id=45657

    • Related Report
      2013 Final Research Report
  • [Remarks] 研究トピックス

    • URL

      http://seesaawiki.jp/w/moriorg3/d/Topics?wiki_id=45657

    • Related Report
      2013 Annual Research Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

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