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Research and development of organocatalyst as an artificial acylating enzyme

Research Project

Project/Area Number 15K18838
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionTokyo University of Pharmacy and Life Science

Principal Investigator

NAKASHIMA Kosuke  東京薬科大学, 薬学部, 助手 (90722843)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords有機触媒 / 不斉合成 / フルオラス / 有機分子触媒
Outline of Final Research Achievements

I constructed an organocatalyst library having various sulfonamide type structures derived from natural amino acids for the purpose of developing an artificial acylating catalyst. The optical resolution reaction of phenylethane-1,2-diol performed as a model reaction did not give good results. Therefore, I studied stereoselective carbon-carbon bond formation reaction using this organocatalyst library. As a result, good results were obtained in asymmetric conjugate addition reaction of α, β-unsaturated ketone and nitroalkane, and direct-vinylogous aldol reaction between γ-crotonolactone and aldehyde.

Report

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

    (13 results)

All 2017 2016 2015

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (7 results)

  • [Journal Article] Design of Novel Hydrogen-Bonding Donor Organocatalysts and their Application to Asymmetric Direct Aldol Reaction2017

    • Author(s)
      H. Akutsu, K. Nakashima, H. Yanai, A. Kotani, S. Hirashima, T. Yamamoto, R. Takahashi, A. Yoshida, Y. Koseki, H. Hakamata, T. Matsumoto, T. Miura,
    • Journal Title

      Synlett

      Volume: 印刷中

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Squaramide-sulfonamide organocatalyst for asymmetric direct vinylogous aldol reactions2017

    • Author(s)
      T. Sakai, S. Hirashima, Y. Yamashita, R. Arai, K. Nakashima, A. Yoshida, Y. Koseki, T. Miura,
    • Journal Title

      J. Org. Chem

      Volume: 82 Issue: 9 Pages: 4661-4667

    • DOI

      10.1021/acs.joc.7b00287

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective conjugate addition of carbonyl compounds to maleimides using diaminomethyleneindenedione organocatalyst2016

    • Author(s)
      K. Nakashima, M.Kawada, S. Hirashima, A. Kosugi, M. Kato, A. Yoshida, Y. Koseki, T. Miura
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 27 Pages: 888-895

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmeric chlorination of b-ketoesters using diaminomethylenemalononitrile organocatalyst.2016

    • Author(s)
      T. Sakai, S. Hirashima, K. Nakashima, C. Maeda, A. Yoshida, Y. Koseki, T. Miura
    • Journal Title

      Chem. Pharm. Bull

      Volume: 64 Pages: 1781-1784

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Conjugate Addition of Ketones to Maleimides Using Diaminomethyleneindenedione Organocatalyst2015

    • Author(s)
      Kosuke Nakashima, Masahiro Kawada, Shin-ichi Hirashima, Mana Kato, Yuji Koseki, Tsuyoshi Miura*
    • Journal Title

      Synlett

      Volume: 09 Issue: 09 Pages: 1248-1252

    • DOI

      10.1055/s-0034-1380382

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrophosphonylation of Aldehydes using a Cinchona–Diaminomethylenemalononitrile Organocatalyst2015

    • Author(s)
      Shin-ichi Hirashima, Ryoga Arai, Kosuke Nakashima, Nobuaki Kawai, Junko Kondo, Yuji Koseki andTsuyoshi Miura*
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 18 Issue: 18 Pages: 3863-3867

    • DOI

      10.1002/adsc.201500816

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] 有機分子触媒を用いたα-シアノケトンのエノンへの不斉共役付加反応の開発2017

    • Author(s)
      〇野田優太、中島康介、平島真一、古石裕治、三浦剛
    • Organizer
      日本薬学会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Annual Research Report
  • [Presentation] 有機分子触媒を用いた5-アルキルフルフラール誘導体の不斉ε位アルキル化反応2017

    • Author(s)
      〇阿久津裕士、中島康介、北原萌子、平島真一、古石裕治、三浦剛
    • Organizer
      日本薬学会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Annual Research Report
  • [Presentation] スルホンアミド-チオウレア型有機分子触媒を用いた不斉反応2016

    • Author(s)
      〇河田雅弘、中島康介、平島真一、坂上徹、鈴木智博、野田優太、吉田彰宏、古石裕治、三浦剛
    • Organizer
      反応と合成の進歩シンポジウム
    • Place of Presentation
      静岡
    • Year and Date
      2016-11-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] 有機分子触媒を用いたカルボニル化合物のマレイミドへの不斉共役付加反応2016

    • Author(s)
      〇河田雅弘、中島康介、平島真一、小杉綾子、加藤真奈、吉田彰宏、古石裕治、三浦剛
    • Organizer
      創薬懇話会
    • Place of Presentation
      蓼科
    • Year and Date
      2016-06-30
    • Related Report
      2016 Annual Research Report
  • [Presentation] 新規水素結合供与型有機分子触媒の設計と不斉アルドール反応への適用2016

    • Author(s)
      ◯阿久津 裕士、山本 智之、中島 康介,矢内 光、高橋 流太、小谷 明、平島 真一、古石 裕治、袴田 秀樹、松本 隆司、三浦 剛
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 新規有機分子触媒を用いたアルキリデンマロン酸エステルへの不斉共役付加反応の開発2016

    • Author(s)
      河田 雅宏、◯坂上 徹、中島 康介、平島 真一古石 裕治、三浦 剛
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] フルオラス有機分子触媒を用いたフラン誘導体の不斉アルキル化反応2016

    • Author(s)
      〇阿久津裕士、中島康介、平島真一、吉田彰宏、古石裕治、三浦剛
    • Organizer
      フルオラス科学研究会
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report

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

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