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Development of Combo Metal Catalysis for Rapid 1,3-Rearrangement of Propargyl Alcohols and Its Application to Efficient Transformations

Research Project

Project/Area Number 20790015
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionUniversity of Shizuoka

Principal Investigator

EGI Masahiro  University of Shizuoka, 薬学部, 講師 (80363901)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2008: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords複合触媒 / 転位反応 / 連続反応 / 固定化触媒 / 環境調和 / 合成化学 / 触媒・化学プロセス / フラン / ピロール / カチオン性金触媒
Research Abstract

I have disclosed that the combination of MoO2(acac)2, (Ph3P)AuCl, and AgOTf provides a powerful catalytic system for the rapid 1,3-rearrangement of propargyl alcohols. The reactions proceed at room temperature within 1 h in most cases to afford a variety of α,β-unsaturated carbonyl compounds in excellent yields. During the further study on its application to various substrates, it was found that the cationic gold-catalyzed intramolecular cyclizations of the propargyl alcohols having carbonyl, hydroxyl, or amino groups gave the heterocyclic compounds, such as 3(2H)-furanones, furanes, and pyrroles. A polymer-supported cationic gold compound was also synthesized and showed high reactivity. It was recovered quantitatively from the reaction mixture by simple filtration and reused for four runs.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (18 results)

All 2010 2009 2008

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (12 results)

  • [Journal Article] Cationic Gold(I)-Catalyzed Intramolecular Cyclization ofγ-Hydroxyalkynones into 3(2H)-Furanones2010

    • Author(s)
      江木正浩、畦地健司、實藤盛朗、清水薫、赤井周司
    • Journal Title

      The Journal of Organic Chemistry 75

      Pages: 2123-2126

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Cationic Gold (I)-Catalyzed Intramolecular Cyclization of γ-Hydroxy-alkvnones into 3 (2H)-Furanones2010

    • Author(s)
      Masahiro Egi
    • Journal Title

      The Journal of Organic Chemistry 75

      Pages: 2123-2126

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cationic Gold(I)-Mediated Intramolecular Cyclization of 3-Alkyne-1, 2-diols and 1-Amino- 3-alkyn-2-ols: A Practical Route to Furans and Pyrroles2009

    • Author(s)
      江木正浩、畦地健司、赤井周司
    • Journal Title

      Organic Letters 11

      Pages: 5002-5005

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Cationic Gold (I)-Mediated Intramolecular Cyclization of 3-Allcyne-1, 2-diols and 1-Amino-3-alkyn-2-ols : A Practical Route to Furans and Pyrroles2009

    • Author(s)
      Masahiro Egi
    • Journal Title

      Organic Letters 11

      Pages: 5002-5005

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Mo-Au Combo Catalysis for Rapid 1, 3-Rearrangement of Propargyl Alcohols intoα, β-Unsaturated Carbonyl Compounds2008

    • Author(s)
      江木正浩、山口淑子、藤原登、赤井周司
    • Journal Title

      Organic Letters 10

      Pages: 1867-1870

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Mo-Au Combo Catalysis for Rapid 1, 3-Rearrangement of Propargyl Alcohols into α, β-Unsaturated Carbonyl Compounds2008

    • Author(s)
      Masahiro Egi
    • Journal Title

      Organic Letters 10

      Pages: 1867-1870

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] カチオン性金触媒を用いるγ-ヒドロキシアルキノン類の分子内環化反応2010

    • Author(s)
      江木正浩、清水薫、畦地健司、赤井周司
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] カチオン性金触媒によるホモプロパルギルアルコール及びアミン化合物の分子内閉環反応:フラン及びピロール類の簡便で効率的な合成2009

    • Author(s)
      江木正浩、畦地健司、赤井周司
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Year and Date
      2009-11-17
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] カチオン性金触媒による複素環化合物の効率的かつ環境低負荷型合成2009

    • Author(s)
      江木正浩、畦地健司、赤井周司
    • Organizer
      日本プロセス化学会2009サマーシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2009-07-16
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] カチオン性金触媒によるω-ヒドロキシアルキニルエーテルの分子内閉環反応:不飽和ラクトン類の効率的合成2009

    • Author(s)
      江木正浩、西村友香、畦地健司、赤井周司
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-28
    • Related Report
      2009 Final Research Report
  • [Presentation] カチオン性金触媒によるω-ヒドロキシアルキニルエーテルの分子内閉環反応 : 不飽和ラクトン類の効率的合成2009

    • Author(s)
      江木正浩
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] リサイクル型カチオン性金触媒による複素環化合物の効率的かつ環境低負荷型合成2008

    • Author(s)
      江木正浩、畦地健司、赤井周司
    • Organizer
      平成20年度日本薬学会東海支部例会
    • Place of Presentation
      静岡
    • Year and Date
      2008-12-06
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] カチオン性金触媒を用いるプロパルギルケトン化合物の分子内環化反応:フラノン類の効率的合成2008

    • Author(s)
      江木正浩、實藤盛朗、赤井周司
    • Organizer
      平成20年度日本薬学会東海支部例会
    • Place of Presentation
      静岡
    • Year and Date
      2008-12-06
    • Related Report
      2009 Final Research Report
  • [Presentation] カチオン性金触媒を用いるプロパルギルケトン化合物の分子内環化反応 : フラノン類の効率的合成2008

    • Author(s)
      江木正浩
    • Organizer
      平成20年度日本薬学会東海支部例会
    • Place of Presentation
      静岡
    • Year and Date
      2008-12-06
    • Related Report
      2008 Annual Research Report
  • [Presentation] Mo-Au Combo Catalysis for Rapid 1, 3-Rearrangement of Propargyl Alcohols intoα, β-Unsaturated Carbonyl Compounds2008

    • Author(s)
      江木正浩、藤原登、山口淑子、赤井周司
    • Organizer
      The First International Symposium on Process Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2008-07-29
    • Related Report
      2009 Final Research Report
  • [Presentation] Mo-Au Combo Catalysis for Rapid 1, 3-Rearrangement of Propargyl Alcohols into α, β-Unsaturated Carbonyl Compounds2008

    • Author(s)
      Masahiro Egi
    • Organizer
      The First International Symposium on Process Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2008-07-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] カチオン性金触媒によるホモプロパルギルアルコール及びアミン化合物の分子内閉環反応;フラン及びピロール類の効率的合成2008

    • Author(s)
      江木正浩、畦地健司、赤井周司
    • Organizer
      第54回日本薬学会東海支部総会・大会
    • Place of Presentation
      名古屋
    • Year and Date
      2008-07-05
    • Related Report
      2009 Final Research Report
  • [Presentation] カチオン性金触媒によるホモプロパルギルアルコール及びアミン化合物の分子内閉環反応 ; フラン及びピロール類の効率的合成2008

    • Author(s)
      江木正浩
    • Organizer
      第54回日本薬学会東海支部総会・大会
    • Place of Presentation
      名古屋
    • Year and Date
      2008-07-05
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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