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asymmetric C-C bond formation via simultaneous activation by bimetallic catalysts

Research Project

Project/Area Number 16K18857
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionMicrobial Chemistry Research Foundation

Principal Investigator

SAITO Akira  公益財団法人微生物化学研究会, 微生物化学研究所, 研究員 (10772866)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsアリル化 / 不斉合成 / アミド / 含フッ素化合物 / 協奏機能触媒 / 協奏機能型触媒 / 触媒的不斉合成 / アリル化反応 / エノラート / パラジウム触媒
Outline of Final Research Achievements

Catalytic asymmetric a-allylation of a-CF3 amide was developed by the design of novel synergistic catalyst system, which nucleophilic 7-azaindoline amide enolate by chiral Cu/hard Bronsted base and electrophilic pi-allyl Pd species can be independently generated and coexist. The novel methodology of enantioselective C-C bond formation at a-position of amides, whose alpha-deprotonation is regarded difficult in general, could be successfully presented. The chiral alpha-CF3-gamma,delta-unsaturated amides obtained by the reaction can be transformed to corresponding CF3-substituted cyclopropane derivatives, which are promising building block for drug candidate in the field of medicinal chemistry.

Report

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

    (7 results)

All 2018 2017 2016 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results,  Acknowledgement Compliant: 1 results) Presentation (4 results) (of which Int'l Joint Research: 1 results) Remarks (2 results)

  • [Journal Article] Cu/Pd Synergistic Dual Catalysis: Asymmetric a-Allylation of an a-CF3 Amide2017

    • Author(s)
      Akira Saito, Naoya Kumagai, Masakatsu Shibasaki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 20 Pages: 5551-5555

    • DOI

      10.1002/anie.201702113

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] シアノ基の求電子的多重活性化を指向した2核金属錯体の合成研究2018

    • Author(s)
      齊藤 誠、熊谷 直哉、柴﨑 正勝
    • Organizer
      日本薬学会第138年会(金沢)
    • Related Report
      2017 Annual Research Report
  • [Presentation] Cu/Pdバイナリー型触媒を用いたα-CF3アミドのα-不斉アリル化反応2017

    • Author(s)
      齊藤誠、熊谷直哉、柴崎正勝
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学川内北キャンパスC棟2F C205(宮城県仙台市)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] Asymmetric α-Allylation of α-CF3 Amide Promoted by Cu/Pd Synergistic Catalyst2017

    • Author(s)
      Akira Saito, Naoya Kumagai, Masakatsu Shibasaki
    • Organizer
      OMCOS19
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Cu/Pdバイメタリック触媒によるα-CF3アミドのα-不斉アリル化反応2016

    • Author(s)
      齊藤誠、熊谷直哉、柴崎正勝
    • Organizer
      第109回有機合成シンポジウム
    • Place of Presentation
      東京工業大学(東京都目黒区)
    • Year and Date
      2016-06-08
    • Related Report
      2016 Research-status Report
  • [Remarks] 公益財団法人微生物化学研究会

    • URL

      http://www.bikaken.or.jp/

    • Related Report
      2017 Annual Research Report
  • [Remarks] IMC 微生物化学研究所

    • URL

      http://www.bikaken.or.jp

    • Related Report
      2016 Research-status Report

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

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