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Development of Asymmetric Organo Acid Catalyst Possessing Perfluorophenyl Group for Allylation Reaction

Research Project

Project/Area Number 21750087
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionTohoku University

Principal Investigator

MOMIYAMA Norie  Tohoku University, 大学院・理学研究科, 助教 (80447127)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords不斉合成 / 反応 / ブレンステッド酸 / アリル化反応 / イミン / アリルシラン / クロチルシラン / アリル化
Research Abstract

The present study was conducted based on the development of chiral organo acid catalyst for enantioselective synthesis of homoallylamines. We successfully synthesized chiral phosphoric acid catalyst possessing pentafluorophenyl group for highly enantioselective Hosomi-Sakurai allylation reaction of imines with allyltrimethylsilanes. When the reaction was conducted with 3,5-di-tert-butyl benzoyl mine in the presence of 20 mol% chiral binaphtol derived phosphoric acid and 80mol% biphenol derived phosphoric acid, the homoallylamines were obtained in good yields with high enantioselectivites (90-99% ee).

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (8 results)

All 2011 2010

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

  • [Journal Article] Chiral Bronsted Acid Catalysis for Enantioselective Hosomi-Sakurai Reaction of Imines with Allyltrimethylsilane2011

    • Author(s)
      Momiyama, N., Nishimoto, H., Terada, M.
    • Journal Title

      Organic Letters 13

      Pages: 2126-2129

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Bronsted Acid Catalysis for Enantioselective Hosomi-Sakurai Reaction of Imines with Allyltrimethylsilane2011

    • Author(s)
      Norie Momiyama, Hayato Nishimoto, Masahiro Terada
    • Journal Title

      Organic Letters

      Volume: 8 Pages: 2126-2129

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] キラルブレンステッド酸触媒によるイミン類へのジアステレオかつエナンチオ選択的細見-櫻井アリル化反応2010

    • Author(s)
      西本隼人・椴山儀恵・寺田眞浩
    • Organizer
      第3回有機触媒シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2010-09-24
    • Related Report
      2010 Final Research Report
  • [Presentation] Chiral Bronsted Acid Promoted Enantioselective Allylation of Allyltrimethyl silane to Imines2010

    • Author(s)
      Nishimoto, Hayato, Momiyama, Norie, Terada, Masahiro
    • Organizer
      東北大学Global COE Program Summer School
    • Place of Presentation
      仙台
    • Year and Date
      2010-08-19
    • Related Report
      2010 Final Research Report
  • [Presentation] キラルブレンステッド酸触媒によるイミン類へのジアステレオかつエナンチオ選択的細見-櫻井アリル化反応2010

    • Author(s)
      西本隼人・椴山儀恵・寺田眞浩
    • Organizer
      第21回万有仙台シンポジウム ポスター賞
    • Place of Presentation
      仙台
    • Year and Date
      2010-06-05
    • Related Report
      2010 Final Research Report
  • [Presentation] キラルブレンステッド酸触媒によるイミン類へのジアステレオかつエナンチオ選択的細見-櫻井アリル化反応2010

    • Author(s)
      西本隼人, 椴山儀恵, 寺田眞浩
    • Organizer
      第21回万有仙台シンポジウム
    • Place of Presentation
      仙台国際センター
    • Year and Date
      2010-06-05
    • Related Report
      2010 Annual Research Report
  • [Presentation] キラルブレンステッド酸触媒によるイミン類へのジアステレオかつエナンチオ選択的細見-櫻井アリル化反応2010

    • Author(s)
      西本隼人・椴山儀恵・寺田眞浩
    • Organizer
      日本化学会第90春季年会、1F5-47
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] キラルブレンステッド酸によるイミン類へのジアスレレオかつエナンチオ選択的細見-櫻井アリル化反応2010

    • Author(s)
      西本隼人
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      2010-03-26
    • Related Report
      2009 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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