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Development and Application of Novel Chiral Ionic Bronsted Acid

Research Project

Project/Area Number 21750095
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

URAGUCHI Daisuke  Nagoya University, 工学研究科, 講師 (70426328)

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: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2009: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywords合成有機化学 / 有機触媒 / 有機分子触媒 / ブレンステッド酸 / 共役付加 / 有機イオン対 / 不斉合成 / 触媒反応 / プロトネーション
Research Abstract

A series of novel chiral ionic Bronsted acids, P-spiro chiral tetraaminophosphonium barfate, have been developed. These chiral salts were found to be an effective catalyst for hetero-Michael addition to nitroolefins with highly enantioselective manner, which is regarded as one of the challenging transformations. The products of these reactions are useful chiral intermediate of biologically relevant molecules. Further, the acidity of the salt was successfully enhanced trough the appropriate structural modification.

Report

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

    (20 results)

All 2011 2010 2009

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (14 results)

  • [Journal Article] EnantiosEnantiose lective Aza-Michael Addition to Conjuga ted Nitroenynes Catalyzed by Chiral Arylaminophosphonium Barfates2011

    • Author(s)
      Uraguchi, Daisuke ; Kinoshita, Natsuko ; Kizu, Tomohito ; Ooi, Takashi
    • Journal Title

      Synlett in press

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Aza-Michael Addition to Conjugated Nitroenynes Catalyzed by Chiral Arylaminophosphonium Barfates2011

    • Author(s)
      Uraguchi, Daisuke ; Kinoshita, Natsuko ; Kizu, Tomohito ; Ooi, Takashi
    • Journal Title

      Synlett

      Volume: (in press)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Prot onation of α-Amino Acid-Derived Ketene Disilyl Acetals Using P-Spiro Diaminod ioxaphosphonium Barfates as Chiral Proton2010

    • Author(s)
      Uraguchi, Daisuke ; Kinoshita, Natsuko ; Ooi, Takashi
    • Journal Title

      urnal of the American Chemical Society 132

      Pages: 12240-12242

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using P-Spiro Diaminodioxaphosphonium Barfates as Chiral Proton2010

    • Author(s)
      Uraguchi, Daisuke ; Kinoshita, Natsuko ; Ooi, Takashi
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 132 Pages: 12240-12242

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Arylaminophosphonium Barfates as a New Class of Charged Bronsted Acid for the Enantioselective Activation of Nonionic Lewis Bases2009

    • Author(s)
      Uraguchi, Daisuke ; Nakashima, Daisuke ; Ooi, Takashi
    • Journal Title

      Journal of the American Chemical Society 131

      Pages: 7242-7243

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Arylaminophosphonium Barfates as a New Class of Charged Bronsted Acid for the Enantioselective Activation of Nonionic Lewis Bases2009

    • Author(s)
      Daisuke Uraguchi, Daisuke Nakashima, Takashi Ooi
    • Journal Title

      Journal of the American Chemical Society 131

      Pages: 7242-7243

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] 光学活性アリールアミノホスホニウムバフェートを触媒とする位置及びエナンチオ選択的プロトン化反応2011

    • Author(s)
      木下奈津子, 浦口大輔, 大井貴史
    • Organizer
      日本化学会第91春季年会 予稿集
    • Year and Date
      2011-03-11
    • Related Report
      2010 Final Research Report
  • [Presentation] 触媒的不斉プロトン化反応によるα-アルコキシカルボン酸の合成2011

    • Author(s)
      木津智仁, 木下奈津子, 浦口大輔, 大井貴史
    • Organizer
      日本化学会第91春季年会 予稿集
    • Year and Date
      2011-03-11
    • Related Report
      2010 Final Research Report
  • [Presentation] 光学活性アリールアミノホスホニウムバフェートを触媒とする位置及びエナンチオ選択的プロトン化反応2011

    • Author(s)
      木下奈津子, 浦口大輔, 大井貴史
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (予稿集)
    • Year and Date
      2011-03-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] 触媒的不斉プロトン化反応によるα-アルコキシカルボン酸の合成2011

    • Author(s)
      木津智仁, 木下奈津子, 浦口大輔, 大井貴史
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (予稿集)
    • Year and Date
      2011-03-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] 光学活性ジアミノジオキサホスホニウムバフェートを触媒とした不斉プロトン化反応2010

    • Author(s)
      木下奈津子, 浦口大輔, 大井貴史
    • Organizer
      第41回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋技術科学大学
    • Year and Date
      2010-11-07
    • Related Report
      2010 Final Research Report
  • [Presentation] 光学活性ジアミノジオキサホスホニウムバフェートを触媒とした不斉プロトン化反応2010

    • Author(s)
      木下奈津子, 浦口大輔, 大井貴史
    • Organizer
      第41回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋技術科学大学 愛知県豊橋市
    • Year and Date
      2010-11-07
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric Thio-Michael Reaction to Nitroolefin Catalyzed by Axially2010

    • Author(s)
      木下奈津子, 浦口大輔, 大井貴史
    • Organizer
      Chiral Cationic Bronsted Acid、Nagoya University Global COE in Chemistry, 3rd Annual Symposium
    • Place of Presentation
      名古屋大学
    • Year and Date
      2010-06-16
    • Related Report
      2010 Final Research Report
  • [Presentation] Asymmetric Thio-Michael Reaction to Nitroolefin Catalyzed by Axially Chiral Cationic Bronsted Acid2010

    • Author(s)
      木下奈津子, 浦口大輔, 大井貴史
    • Organizer
      Nagoya University Global COE in Chemistry, 31^<rd> Annual Symposium
    • Place of Presentation
      野依記念学術交流館 愛知県名古屋市
    • Year and Date
      2010-06-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using Enantiomerically Pure P-Spiro Aminophosphonium Barfate as Chiral Proton2010

    • Author(s)
      木下奈津子, 浦口大輔, 大井貴史
    • Organizer
      22nd International Symposium on Chirality (ISCD-22): Chirality 2010
    • Place of Presentation
      札幌コンベンションセンター
    • Related Report
      2010 Final Research Report
  • [Presentation] アリールアミノホスホニウムボレートを触媒とした不斉プロトン化反応2010

    • Author(s)
      木下奈津子、浦口大輔、大井貴史
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] 光学活性アリールアミノホスホニウムボレートをカチオン性Bronsted酸触媒とする不斉共役付加反応2010

    • Author(s)
      中島大輔、浦口大輔、大井貴史
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using Enantiomerically Pure P-Spiro Aminophosphonium Barfate as Chiral Proton2010

    • Author(s)
      木下奈津子, 浦口大輔, 大井貴史
    • Organizer
      22^<nd> International Symposium on Chirality (ISCD-22) : Chirality 2010
    • Place of Presentation
      札幌コンベンションセンター 北海道札幌市
    • Related Report
      2010 Annual Research Report
  • [Presentation] 新規カチオン性Bronsted酸の創製と触媒的不斉Aza-Michael付加反応への適用2009

    • Author(s)
      中島大輔、浦口大輔、大井貴史
    • Organizer
      第3回物質科学フロンティアセミナー
    • Place of Presentation
      名古屋大学
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] 光学活性テトラアミノホスホニウムボレートの創製とカチオン性ブレンステッド酸触媒としての機能発現2009

    • Author(s)
      中島大輔、浦口大輔、大井貴史
    • Organizer
      第39回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      岐阜大学
    • Related Report
      2010 Final Research Report 2009 Annual Research Report

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

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