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Generation of metal-carbene species without using diazo-comoounds and its synthetic application

Research Project

Project/Area Number 15K13686
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

MATSUNAGA Shigeki  北海道大学, 薬学研究院, 教授 (50334339)

Research Collaborator SHIGENO Daiki  
MIYAZAWA Taku  
TAKIZAWA Kouji  
SUNADOI Yuta  
SATAKE Shun  
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords遷移金属触媒 / 遷移金属カルベン / 直接変換 / シクロプロパン / コバルト / ルテニウム / シクロプロパン化
Outline of Final Research Achievements

We tried to develop new methods to generate transition metal-carbene species without using diazo compounds. We initially tried direct generation of the transition metal-carbene species from methylene compounds under oxidative conditions; but, all trials failed. Thus, we investigated alternative methods by using iodonium ylides as starting materials. In this case, the reaction proceeded smoothly. Therefore, we then turned our attention to develop new chiral catalysts for stereocontrol using iodonium ylides. After intensive investigation, we finally found chiral Ru complex was the best, giving cyclopropanes in up to 97% enantioselectivity.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (6 results)

All 2017 2016 2015 Other

All Presentation (5 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results) Remarks (1 results)

  • [Presentation] カルボニルイリドの分子間1,3-双極付加環化反応を機軸とするフロンドシンAの触媒的不斉合成研究2017

    • Author(s)
      滝沢昂嗣、砂土居裕太、穴田仁洋、松永茂樹、橋本俊一
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学(宮城県・仙台市)
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
  • [Presentation] 化学変換における高い原子効率の実現を指向した 第一列遷移金属触媒の設計2017

    • Author(s)
      松永茂樹
    • Organizer
      CSJフェスタ
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 二核ロジウム(II)カルボキシラート錯体を用いたα-ジアゾエステルの分子内C-H挿入反応の開発2016

    • Author(s)
      宮澤拓、穴田仁洋、松永茂樹、橋本俊一
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      清水文化会館マリナート(静岡県・静岡市)
    • Year and Date
      2016-11-07
    • Related Report
      2016 Research-status Report
  • [Presentation] Enantio- and diastereoselective intramolecular C-H insertion reaction of a-diazoesters catalyzed by chiral dirhodium(II) carboxylates2016

    • Author(s)
      T. Miyazawa, K. Minami, K. Imai, K. Takeda, M. Anada, S. Matsunaga, S. Hashimoto
    • Organizer
      T. Miyazawa, K. Minami, K. Imai, K. Takeda, M. Anada, S. Matsunaga, S. Hashimoto
    • Place of Presentation
      北海道大学(北海道札幌市)
    • Year and Date
      2016-01-07
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Rh(II)カルボキシラート錯体を用いたアリールジアゾアセタートの分子内不斉シクロプロパン化反応2015

    • Author(s)
      滋野大喜、竹田幸司、穴田仁洋、松永茂樹、橋本俊一
    • Organizer
      第5回CSJフェスタ
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Remarks]

    • URL

      http://www.pharm.hokudai.ac.jp/yakuzou/publication.html

    • Related Report
      2017 Annual Research Report

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Published: 2015-04-16   Modified: 2019-03-29  

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