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Development of new asymmetric phosphenium salt catalysts, and its application to the construction of chiral tetra-substituted carbon.

Research Project

Project/Area Number 20790006
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

HARADA Shinji  Chiba University, 大学院・薬学研究院, 助教 (10451759)

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: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2008: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywords不斉触媒 / 有機合成化学 / 不斉四置換炭素 / ホスフェニウム / ウレア / イッテルビウム / Diels-Alder反応 / 有機化学 / 含窒素化合物 / ウレア型配位子 / ホスフェニウム塩 / ホスフェニウムカチオン / リン
Research Abstract

Phosphorus compounds are known as Lewis basic chemicals, however, cationic phosphines have Lewis acidic character. I focused on phosphenium salts, and I found that they worked as a Lewis acidic catalyst for hetero-Diels-Alder reaction. Although I synthesized a variety of chiral phosphenium salts, catalytic asymmetric reactions were not realized. Meanwhile, I found that one bis-urea compound, which was a synthetic intermediate of chiral phosphenium salt, formed a good complex with Ytterbium to catalyze highly reactive and highly stereoselective Diels-Alder reaction.

Report

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

    (11 results)

All 2010 2009 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results) Presentation (6 results) Remarks (2 results)

  • [Journal Article] Catalytic Enantioselective Total Synthesis of (-)-Platyphyllide and Its Structural Revision2010

    • Author(s)
      Shiharu Hiraoka, Shinji Harada, Atsushi Nishida. *
    • Journal Title

      J. Org. Chem.

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Highly enantioselective Diels-Alder reaction of Danishefsky-type diene and electron-deficient olefins catalyzed by an Yb(III)/chiral bis-urea complex2009

    • Author(s)
      Shinji Harada, Nozomi Toudou, Shiharu Hiraoka, Atsushi Nishida*
    • Journal Title

      Tetrahedron Lett. 50

      Pages: 5652-5655

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Highly enantioselective Diels-Alder reaction of Danishefsky-type diene and electron-deficient olefins catalyzed by an Yb(III)/chiral bis-urea complex2009

    • Author(s)
      Shinji Harada
    • Journal Title

      Tetrahedron Letters 50

      Pages: 5652-5655

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] キラルYb錯体を用いたDanishefsky dieneと電子不足オレフィンの触媒的不斉Diels-Alder反応2009

    • Author(s)
      西田篤司, 東道のぞみ
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢・金沢市民ホール
    • Year and Date
      2009-11-17
    • Related Report
      2009 Final Research Report
  • [Presentation] キラルYb錯体を用いた Danishefsky diene と電子不足オレフィンの触媒的不斉 Diels-Alder 反応2009

    • Author(s)
      西田篤司
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢・金沢市民ホール
    • Year and Date
      2009-11-17
    • Related Report
      2009 Annual Research Report
  • [Presentation] Asymmetric Diels-Alder Reaction of Danishefsky-Type Diene Catalyzed by Chiral Yb(III) Complex and Its Application to the Total Synthesis of Platyphyllide2009

    • Author(s)
      西田篤司, 平岡紫陽
    • Organizer
      IKCOC-11
    • Place of Presentation
      京都・リーガロイヤルホテル
    • Year and Date
      2009-11-11
    • Related Report
      2009 Final Research Report
  • [Presentation] Asymmetric Diels-Alder Reaction of Danishefsky-Type Diene Catalyzed by Chiral Yb(III)Complex and Its Application to the Total Synthesis of Platyphyllide2009

    • Author(s)
      西田篤司
    • Organizer
      IKCOC-11
    • Place of Presentation
      京都・リーガロイヤルホテル
    • Year and Date
      2009-11-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] Asymmetric Diels-Alder Reaction of Danishefsky Dienes2009

    • Author(s)
      Atsushi Nishida, 西田篤司
    • Organizer
      ICCEOCA-4
    • Place of Presentation
      Bangkok, Thailand
    • Related Report
      2009 Final Research Report
  • [Presentation] Asymmetric Diels-Alder Reaction Using Electron Rich Siloxybutadienes2009

    • Author(s)
      Atsushi Nishida, 西田篤司
    • Organizer
      5th Sino-Japanese Symposium on Organic Chemistry for Young Scientists
    • Place of Presentation
      Chengdu, China
    • Related Report
      2009 Final Research Report
  • [Remarks]

    • URL

      http://www.p.chiba-u.ac.jp/lab/gousei/research3/research3.html

    • Related Report
      2009 Final Research Report
  • [Remarks]

    • URL

      http://www.p.chiba-u.ac.jp/lab/gousei/research3/research3.html

    • Related Report
      2009 Annual Research Report

URL: 

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

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