• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

New Entries to Ring Construction Based on Cycloaddition between Allenyl Bonds and C-C Multiple Bonds

Research Project

Project/Area Number 15K18826
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionKanazawa University

Principal Investigator

YASUDA Shigeo  金沢大学, 薬学系, 助教 (40647038)

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: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2015: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsアレン / C-H活性化 / アルキン / アルケン / ロジウム / 環化反応 / C-C活性化 / 環構築反応 / ロジウム触媒
Outline of Final Research Achievements

In line with the initial plan, (1) development of a cycloisomerization of allene-alkynes via a C-H bond activation, and (2) development of an asymmetric intramolecular [2+2+2] cycloaddition of allene-ene-ynes were attempted. In the study of (1), we were able to develop the planned reaction. In the study of (2), we could not obtain the originally intended results, but succeeded in developing a new cyclization reaction different from the intended reaction. Furthermore, we were able to develop the following two ring-closing reactions in the relevant region, namely the partially intermolecular [2+2+2] cycloaddition of allene-alkynes with alkynes, and the intramolecular [6+2] cycloaddition of allenylazacyclobutane-alkynes.

Report

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

    (19 results)

All 2017 2016 2015

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Acknowledgement Compliant: 5 results) Presentation (14 results) (of which Int'l Joint Research: 2 results,  Invited: 1 results)

  • [Journal Article] Enantioselective Total Synthesis of (+)-Sieboldine A2017

    • Author(s)
      Abd El-Gaber, M. K.; Yasuda, S.; Iida, E.; Mukai, C.
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 2 Pages: 320-323

    • DOI

      10.1021/acs.orglett.6b03416

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Construction of Azabicyclo[6.4.0]dodecatrienes Based on Rhodium(I)-Catalyzed Intramolecular [6+2] Cycloaddition between Azetidine, Allene, and Alkynes2016

    • Author(s)
      Yasuda, S.; Yokosawa, H.; Mukai, C.
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 7 Pages: 805-810

    • DOI

      10.1248/cpb.c16-00178

    • NAID

      130005160067

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Chemo- and Regioselective Rhodium(I)-Catalyzed [2+2+2] Cycloaddition of Allenynes with Alkynes.2016

    • Author(s)
      Yasuda, S.; Kawaguchi, Y.; Okamoto, Y.; Mukai, C.
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 34 Pages: 12181-12188

    • DOI

      10.1002/chem.201602239

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Construction of Hexahydrophenanthrenes By Rhodium(I)-Catalyzed Cycloisomerization of Benzylallene-Internal Alkynes through C-H Activation2016

    • Author(s)
      Kawaguchi, Y.; Yasuda, S.; Mukai, C.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 35 Pages: 10473-10477

    • DOI

      10.1002/anie.201605640

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rh<sup>I</sup>-Catalyzed Cycloaddition between Allenyl π-Bonds and C-C Triple Bonds2016

    • Author(s)
      C. Mukai, S. Yasuda
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 74 Issue: 11 Pages: 1108-1118

    • DOI

      10.5059/yukigoseikyokaishi.74.1108

    • NAID

      130005433323

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] (+)-Sieboldine A の不斉全合成2017

    • Author(s)
      Mohammed K. Abd El-Gaber, 安田 茂雄, 飯田 英介, 向 智里
    • Organizer
      日本薬学会 第137年会
    • Place of Presentation
      仙台国際センター・東北大学 宮城
    • Year and Date
      2017-03-24
    • Related Report
      2016 Annual Research Report
  • [Presentation] アレン-アルケン-アルキンの分子内環化付加反応2017

    • Author(s)
      向 智里, 黒川 桂, 横澤 春奈, 長田 亜紗実, 太田 有羽, 河口 康晃, 安田 茂雄
    • Organizer
      日本薬学会 第137年会
    • Place of Presentation
      仙台国際センター・東北大学 宮城
    • Year and Date
      2017-03-24
    • Related Report
      2016 Annual Research Report
  • [Presentation] アレン-アルキン-アルキンの[2+2+2]環化付加反応と付加体の骨格転位反応2017

    • Author(s)
      河口 康晃, 安田 茂雄, 岡本 悠大, 藪下 絢矢, 岩田 隆, 川村 美帆, 向 智里
    • Organizer
      日本薬学会 第137年会
    • Place of Presentation
      仙台国際センター・東北大学 宮城
    • Year and Date
      2017-03-24
    • Related Report
      2016 Annual Research Report
  • [Presentation] アレンを基軸とする新規環構築法2017

    • Author(s)
      安田 茂雄
    • Organizer
      第2回 有機化学シンポジウム
    • Place of Presentation
      京都大学 京都
    • Year and Date
      2017-02-11
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] ロジウム(I)触媒を用いるアレニルアゼチジン-アルキンの分子内[6+2]環化付加反応:アザビシクロ[6.4.0]骨格の構築2016

    • Author(s)
      安田 茂雄, 横澤 春奈, 向 智里
    • Organizer
      日本薬学会北陸支部 第128回例会
    • Place of Presentation
      北陸大学 石川
    • Year and Date
      2016-11-27
    • Related Report
      2016 Annual Research Report
  • [Presentation] C-H活性化を経由するアレン-アルキンの環化異性化反応:ヘキサヒドロフェナントレン骨格の構築2016

    • Author(s)
      河口 康晃, 安田 茂雄, 向 智里
    • Organizer
      第42回 反応と合成の進歩シンポジウム-ライフサイエンスを志向した理論、反応および合成-
    • Place of Presentation
      静岡市清水文化会館 静岡
    • Year and Date
      2016-11-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] アレニンとアルキンのRh(I)触媒[2+2+2]環化付加反応を利用した多置換ベンゼン誘導体の位置選択的合成2016

    • Author(s)
      安田 茂雄, 河口 康晃, 岡本 悠大, 向 智里
    • Organizer
      第46回 複素環化学討論会
    • Place of Presentation
      金沢歌劇座 石川
    • Year and Date
      2016-09-26
    • Related Report
      2016 Annual Research Report
  • [Presentation] Chemo- and Regioselective Rhodium(I)-Catalyzed [2+2+2] Cycloaddition of Allenynes with Alkynes2016

    • Author(s)
      Shigeo Yasuda, Yasuaki Kawaguchi, Yuta Okamoto, Chisato Mukai
    • Organizer
      27th European Colloquium on Heterocyclic Chemistry
    • Place of Presentation
      Amsterdam, The Netherlands
    • Year and Date
      2016-07-03
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] C-H活性化を経由するアレン-アルキンの環化異性化反応:第四級炭素構築を含む三環性骨格形成2016

    • Author(s)
      河口康晃、安田茂雄、関口和樹、向智里
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      横浜 神奈川
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] アレン-アルキン-アルケン体の分子内[2+2+2]環化付加反応による多環性骨格の構築2016

    • Author(s)
      向智里、黒川桂、太田有羽、河口康晃、安田茂雄
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      横浜 神奈川
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Rh(I)触媒を用いたアレニンとアルキンの位置選択的分子間[2+2+2]環化付加反応2016

    • Author(s)
      向智里、河口康晃、岡本悠大、川村美帆、安田茂雄
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      横浜 神奈川
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Rh(I)触媒を用いたアレニンとアルケンの不斉分子間[2+2+2]環化付加反応2016

    • Author(s)
      安田茂雄、横川有花、向智里
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      横浜 神奈川
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Rh(I)-Catalyzed novel Ring-Closing reaction of Allene-Alkynes2015

    • Author(s)
      Yasuaki Kawaguchi, Shigeo Yasuda, Chisato Mukai
    • Organizer
      The 18th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Sitges Barcelona Spain
    • Year and Date
      2015-06-28
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] ロジウム触媒を用いるアレン-アルキンの新規環構築反応2015

    • Author(s)
      安田茂雄、河口康晃、太田有羽、向智里
    • Organizer
      第13回 次世代を担う有機化学シンポジウム
    • Place of Presentation
      立命館大学 滋賀
    • Year and Date
      2015-05-22
    • Related Report
      2015 Research-status Report

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi