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Construction of Polycyclic Compounds via Rhodacycle Intermediate and Its Application to the Asymmetric S ynthesis

Research Project

Project/Area Number 22790002
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionHokkaido University

Principal Investigator

OONISHI Yoshihiro  北海道大学, 大学院・薬学研究院, 助教 (70399955)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsロジウム / アルキン / アレン / アルデヒド / NHC / 含窒素ヘテロ環カルベン / 環化反応 / ヒドロアシル化 / 環化二量化
Research Abstract

Rh(I)-catalyzed intermolecular cycloaddition of 4-allenals with terminal alkynes proceeds smoothly, giving 6-membered cyclic compounds in good to high yields with high regioselectivities. It was also found that in the case of the chiral allene studied, chirality is almost conserved in the course of the cyclization. During ongoing investigation of this cycloaddition, we discovered another type of cyclization of allenynes with tethered aldehydes.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (23 results)

All 2012 2011 2010 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (18 results) Remarks (1 results)

  • [Journal Article] Rh(I)-Catalyzed Formal [6+2] Cycloaddition of 4-Allenals with Alkynes or Alkenes in a Tether2011

    • Author(s)
      Yoshihiro, Oonishi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 27 Pages: 10-386

    • DOI

      10.1021/ja203824v

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of(-)-Corynantheidine by Nickel-Catalyzed Carboxylative Cyclization of Enynes2011

    • Author(s)
      Takashi Mizuno, Yoshihiro Oonishi, Masanori Takimoto, and Yoshihiro Sato
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 0 Issue: 14 Pages: 2606-2609

    • DOI

      10.1002/ejoc.201100147

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rh(I)-Catalyzed Hydroacylation/Cycloisomerization Cascade Reaction : Application to the Construction of the Tricyclic Core of Guanacastepenes2010

    • Author(s)
      Yoshihiro Oonishi, Ai Taniuchi, and Yoshihiro Sato
    • Journal Title

      Synthesis

      Volume: 2010 Issue: 17 Pages: 2884-2892

    • DOI

      10.1055/s-0030-1258184

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium(I)-Catalyzed Hydroacylation/Cycloisomerization Cascade Reaction : Application to the Construction of the Tricyclic Core of Guanacastepenes2010

    • Author(s)
      大西英博
    • Journal Title

      Synthesis

      Pages: 2884-2892

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Rh(I)触媒による4一アレナールとアルキンの分子間[ 6+2]環化付加反応の開発2012

    • Author(s)
      細谷昭仁,大西英博,佐藤美洋
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2012-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] Rh(I)触媒を用いたアレンインとアルデヒドの分子内[ 2+2+2]環化反応の開発2012

    • Author(s)
      北野喜隆,大西英博,佐藤美洋
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2012-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] Rh(I)触媒によるアレニルアルデヒドとアルキンの不斉[ 2+2+2]環化付加反応の開発2012

    • Author(s)
      齊藤誠,大西英博,佐藤美洋
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2012-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] Rh(I)触媒を用いたアレンインとアルデヒドの環化付加反応:ビシクロ[ 5. 3. 0]デカトリエン骨格の新規構築法の開発2012

    • Author(s)
      横江貴之,細谷昭仁,大西英博,佐藤美洋
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2012-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] Rh(I)触媒による4-アレナールとアルキンの分子間[6+2]環化付加反応の開発2012

    • Author(s)
      細谷昭仁
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2012-03-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] Rh(I)触媒によるアレンインとアルデヒドの分子内[2+2+2]環化付加反応の開発2012

    • Author(s)
      北野喜隆
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2012-03-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] Rh(I)触媒によるアレニルアルデヒドとアルキンの不斉[2+2+2]環化付加反応の開発2012

    • Author(s)
      齋藤誠
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2012-03-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] Rh(I)触媒を用いたアレンインとアルデヒドの環化付加反応:ビシクロ[5.3.0]デカトリエン骨格の新規構築法の開発2012

    • Author(s)
      横江貴之
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2012-03-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] Rh(I)触媒によるsp^3 C-H結合活性化を経由するアレンインの環化反応2011

    • Author(s)
      北野喜隆,大西英博,佐藤美洋
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      名古屋大学(名古屋市)
    • Year and Date
      2011-09-08
    • Related Report
      2011 Final Research Report
  • [Presentation] Rh(I)触媒によるsp3 C-H結合活性化を経由するアレンインの環化反応2011

    • Author(s)
      北野喜隆
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学(名古屋市)
    • Year and Date
      2011-09-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] Rh(I)一触媒を用いたアレンインの三員環形成を伴う環化反応の開発2011

    • Author(s)
      北野喜隆,大西英博,佐藤美洋
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      ツインメッセ静岡(静岡)
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] Rh(I)触媒によるアレニルアルデヒドのヒドロアシル化反応の開発2011

    • Author(s)
      木村雄輝,佐々木隆行,大西英博,佐藤美洋
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      ツインメッセ静岡(静岡)
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] Rh(I)-触媒を用いたアレンインの三員環形成を伴う環化反応の開発2011

    • Author(s)
      北野喜隆
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      ツインメッセ静岡(静岡)
    • Year and Date
      2011-03-31
    • Related Report
      2010 Annual Research Report
  • [Presentation] Rh(I)触媒によるアレニルアルデヒドの分子内環化反応の開発2010

    • Author(s)
      大西英博,細谷昭仁,木村雄輝,佐々木隆行,佐藤美洋
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      ウインクあいち(愛知)
    • Year and Date
      2010-11-01
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] Rh(I)-catalyzed Intramolecular Hydroacylation of Allenyl Aldehyde2010

    • Author(s)
      大西英博,佐々木隆行,木村雄輝,佐藤美洋
    • Organizer
      24th International Conference on Organometallic Chemistry(ICOMC2010)
    • Place of Presentation
      Taipei International Convention Center(台湾)
    • Year and Date
      2010-07-22
    • Related Report
      2011 Final Research Report
  • [Presentation] Rh(I)-Catalyzed Cyclization of Allenyl Aldehyde and Tethered Alkyne2010

    • Author(s)
      細谷昭仁,大西英博,佐藤美洋
    • Organizer
      24th International Conference on Organometallic Chemistry(ICOMC2010)
    • Place of Presentation
      Taipei International Convention Center(台湾)
    • Year and Date
      2010-07-22
    • Related Report
      2011 Final Research Report
  • [Presentation] Rh(I)-Catalyzed Cyclization of Allenyl Aldehyde and Tethered Alkyne2010

    • Author(s)
      細谷昭仁
    • Organizer
      24th International Conference on Organometallic Chemistry (ICOMC2010)
    • Place of Presentation
      Taipei International Convention Center(台湾)
    • Year and Date
      2010-07-22
    • Related Report
      2010 Annual Research Report
  • [Presentation] Rh(I)-catalyzed Intramolecular Hydroacylation of Allenyl Aldehyde2010

    • Author(s)
      大西英博
    • Organizer
      24th International Conference on Organometallic Chemistry (ICOMC2010)
    • Place of Presentation
      Taipei International Convention Center(台湾)
    • Year and Date
      2010-07-22
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://gouka.pharm.hokudai.acjp/index.html

    • Related Report
      2011 Final Research Report

URL: 

Published: 2010-08-23   Modified: 2016-04-21  

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