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Synthetic Study on Chirality Control with Circular Polarized Microwave

Research Project

Project/Area Number 15K13700
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

Yamada Tohru  慶應義塾大学, 理工学部(矢上), 教授 (40296752)

Co-Investigator(Kenkyū-buntansha) 今枝 健一  中部大学, 工学部, 教授 (60314085)
Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsキラリティ / マイクロ波 / 円偏波 / 不斉還元 / 軸不斉 / 触媒的不斉合成反応 / キラリティー / 円偏波マイクロ波
Outline of Final Research Achievements

The effect of circularly polarized microwave irradiation was examined. Substrate was charged, without irradiation, or under right-handed / left-handed CPM irradiation, and the ee of the reduced product was analyzed. When the asymmetric catalysis was irradiated with 12.4 GHz CPM, the ee under the right-handed conditions was improved more than the non-irradiated conditions, but decreased in the left-handed conditions. In the 2.45 GHz / 50 W CPM irradiation to the racemic catalytic reaction, both the right-handed and the left-handed conditions improved, and the microwave effect should be considered.
The CPM effect on atropo-isomerization reaction was examined. After 2.45 GHz / 20 W CPM irradiation, the ee was analyzed after reduction to prevent from racemization. As a result of the statistical processing, we found reaction conditions that the enantiomeric excess was observed in the opposite directions on the left-handed and the right-handed, though in the racemic 95% confidence interval.

Report

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

    (16 results)

All 2017 2016 2015

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (12 results) (of which Int'l Joint Research: 3 results,  Invited: 6 results)

  • [Journal Article] Microwave Enhancement on Ring-closing Metathesis of Macrocyclic Bisazole2017

    • Author(s)
      T. Sawada, S. Tashima, K. Saito, T. Yamada
    • Journal Title

      Chem. Lett.

      Volume: 46 Issue: 2 Pages: 274-276

    • DOI

      10.1246/cl.160982

    • NAID

      130005317079

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Microwave Specific Effect on Catalytic atropo-Enantioselective Ring-Opening Reaction of Biaryl Lactones2016

    • Author(s)
      S. Tashima, K. Nushiro, K. Saito, T. Yamada
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 89 Issue: 7 Pages: 833-835

    • DOI

      10.1246/bcsj.20160104

    • NAID

      130005253034

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Microwave Specific Effect on Catalytic Enantioselective Conia-Ene Reaction2016

    • Author(s)
      S. Tashima, T. Sawada, K. Saito, T. Yamada
    • Journal Title

      Chem. Lett.

      Volume: 45 Issue: 6 Pages: 649-651

    • DOI

      10.1246/cl.160200

    • NAID

      130005155051

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Microwave Specific Effect on Catalytic atropo-Enantioselective Ring-Opening Reaction of Biaryl Lactones2016

    • Author(s)
      S. Tashima, K. Nushiro, K. Saito, T. Yamada
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 印刷中

    • NAID

      130005253034

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] Microwave Effect on Enantioselective Catalysis2017

    • Author(s)
      T. Yamada
    • Organizer
      10th CaRLa Winter School
    • Place of Presentation
      Deutsch Amerikanisches Institut (Heidelberg, Germany)
    • Year and Date
      2017-02-12
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] マイクロ波加熱:熱的効果だけじゃない反応加速2017

    • Author(s)
      山田 徹
    • Organizer
      マイクロ波による有機合成反応と生化学分野への適用~マイクロ波の特殊効果について(全2題)
    • Place of Presentation
      豊田中研(愛知県長久手市)
    • Year and Date
      2017-01-20
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Microwave Effect on Enantioselective Catalysis2016

    • Author(s)
      T. Yamada
    • Organizer
      C&FC2016 (Catalysis and Fine Chemicals 2016)
    • Place of Presentation
      Howard Civil Service International House (Taipei, R.O.C.)
    • Year and Date
      2016-11-10
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 不斉還元反応における12.4 GHz円偏波マイクロ波効果2016

    • Author(s)
      坪井克、原園久生、今枝健一、山田徹、堤内要
    • Organizer
      第47回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋技術科学大学(愛知県豊橋市)
    • Year and Date
      2016-11-05
    • Related Report
      2016 Annual Research Report
  • [Presentation] 超熱的効果:マイクロ波合成有機化学の新しいパラダイム2016

    • Author(s)
      山田 徹
    • Organizer
      電磁波励起反応場第188委員会 平成28年度第1回全体委員会 講演会
    • Place of Presentation
      東京工業大学(東京都目黒区)
    • Year and Date
      2016-06-13
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 有機合成反応におけるマイクロ波照射の特異効果の検証2016

    • Author(s)
      田島繁希、山田 徹
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学 京田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Application of circularly polarized microwave to asymmetric synthesis2015

    • Author(s)
      K. Imaeda, K. Ohtake and T. Yamada
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Honolulu(USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Microwave Effect on Enantioselective Catalysis of Biaryl Lactones2015

    • Author(s)
      T. Yamada
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Honolulu(USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Non-thermal Effect of Microwave Assisted Catalytic Enantioselective Reactions,2015

    • Author(s)
      T. Yamada
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Honolulu(USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 有機合成反応におけるマイクロ波照射の特異効果の検証2015

    • Author(s)
      田島繁希、山田 徹
    • Organizer
      第 70 回記念有機合成化学協会関東支部シンポジウム ― 新潟(長岡)シンポジウム―
    • Place of Presentation
      長岡工業高等専門学校 (新潟件長岡市)
    • Year and Date
      2015-11-21
    • Related Report
      2015 Research-status Report
  • [Presentation] ラセミ触媒を用いた不斉還元反応への円偏波マイクロ波効果2015

    • Author(s)
      大竹一輝、今枝健一、堤内 要、山田 徹
    • Organizer
      第9回日本電磁波エネルギー応用学会シンポジウム
    • Place of Presentation
      上智大学(東京都千代田区)
    • Year and Date
      2015-11-19
    • Related Report
      2015 Research-status Report
  • [Presentation] アセトフェノンおよびその誘導体の不斉還元反応への円偏波マイクロ波効果2015

    • Author(s)
      清水颯一郎、谷出智裕、今枝健一、堤内 要、山田 徹
    • Organizer
      第9回日本電磁波エネルギー応用学会シンポジウム
    • Place of Presentation
      上智大学(東京都千代田区)
    • Year and Date
      2015-11-19
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2018-03-22  

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