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Search for carbon-carbon bond formation by the use of boranonitrone

Research Project

Project/Area Number 20790018
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionShowa Pharmaceutical University

Principal Investigator

MORITA Nobuyoshi  Showa Pharmaceutical University, 薬学部, 講師 (00433847)

Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2010: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2009: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2008: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords有機化学 / ボラノニトロン / イソキサゾリジン / 1,3-anti-アミノアルコール / 1,3-syn-アミノアルコール / NH-ニトロン / 分子内オキシム-オレフィン環化付加反応 / イソキゾリジン / 分子内オキシムーオレフィン環化付加反応 / N-ボラノニトロン / 1, 3-anti-アミノアルコール / オキシム
Research Abstract

Boranonitrone, generated from protected oxime with BF_3.OE_t2, underwent intermolecular cycloaddition with alkenes to afford the corresponding isoxazolidines in good yields. Interestingly, the cycloaddition of N-borano-C-ethoxycarbonyl nitrone with alkenes gave 3,5-trans-isoxazolidines, whereas the reaction of tent-butyldimethylsilyloximino-N,N-dimethylethane-amide with alkenes afforded 3,5-cis-isoxazolidines. This reaction is very useful for synthesis of 1,3-anti and 1,3-syn aminoalcohols by reductive cleavage of an N-O bond. Additionally, the reaction of N-borano-C-ethoxycarbonyl nitrone with carbon radical species afforded the corresponding hydroxylamines in good yields.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (23 results)

All 2011 2010 2009 2008 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (20 results) Remarks (1 results)

  • [Journal Article] Intermolecular Cycloaddition of N-Boranonitrone with Alkenes.2008

    • Author(s)
      N.Morita, K.Fukui, J.Irikuchi, H.Sato, Y.Takano, I.Okamoto, H.Ishibashi, O, Tamura.
    • Journal Title

      J.Org.Chem. 73

      Pages: 7164-7174

    • NAID

      130006995618

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Intermolecular Cycloaddition of N-Boranonitrone with Alkenes2008

    • Author(s)
      Nobuyoshi Morita
    • Journal Title

      Journal of Organic Chemistry 73

      Pages: 7164-7174

    • NAID

      130006995618

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] C-アミド置換O-TBSオキシムの分子間環化付加反応2011

    • Author(s)
      河野莉奈
    • Organizer
      日本薬学会第131年会 要旨集上にて発表
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-05
    • Related Report
      2010 Final Research Report
  • [Presentation] C-アミド置換O-TBSオキシムの分子間環化付加反応2011

    • Author(s)
      河野莉奈
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡(要旨集上にて発表)
    • Year and Date
      2011-03-05
    • Related Report
      2010 Annual Research Report
  • [Presentation] N-Borano-C-Ethoxycarbonyl Nitrone with Olefins.2010

    • Author(s)
      Nobuyoshi, Morita
    • Organizer
      12^<th> Belgian Organic Synthesis Symposium
    • Place of Presentation
      Namur, Bergium
    • Year and Date
      2010-07-15
    • Related Report
      2010 Final Research Report
  • [Presentation] Stereoselectivity of Intramolecular Cycloaddition of Nitrone Having Allene Moieties2010

    • Author(s)
      Yukari Saito
    • Organizer
      12^<th> Belgian Organic Synthesis Symposium
    • Place of Presentation
      Namur, Bergium
    • Year and Date
      2010-07-15
    • Related Report
      2010 Final Research Report
  • [Presentation] N-Borano-C-Ethoxycarbonyl Nitrone with Olefins2010

    • Author(s)
      森田延嘉
    • Organizer
      12^<th> Belgian Organic Synthesis Symposium
    • Place of Presentation
      University of Namur(FUNDP), Namur, Belgium
    • Year and Date
      2010-07-15
    • Related Report
      2010 Annual Research Report
  • [Presentation] Stereoselectivity of Intermolecular Cucloaddition of Nitrone Having Allene Moieties2010

    • Author(s)
      齋藤由香理
    • Organizer
      12^<th> Belgian Organic Synthesis Symposium
    • Place of Presentation
      University of Namur(FUNDP), Namur, Belgium
    • Year and Date
      2010-07-15
    • Related Report
      2010 Annual Research Report
  • [Presentation] ニトロンとアレン類との分子間環化付加反応における立体選択性2010

    • Author(s)
      齋藤由香理
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] ニトロンとアレン類との分子間環化付加反応における立体選択性2010

    • Author(s)
      齋藤由香理
    • Organizer
      第130年会日本薬学会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] 分子内にアレン類を有するニトロンの環化付加反応2009

    • Author(s)
      齋藤由香理
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟
    • Year and Date
      2009-11-28
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] N-ボラノ-C-エトキシカルボニルニトロンとアルケン類との分子間環化付加反応2009

    • Author(s)
      森田延嘉
    • Organizer
      第39回複素環化学討論会
    • Place of Presentation
      千葉
    • Year and Date
      2009-10-14
    • Related Report
      2010 Final Research Report
  • [Presentation] N-ボラノ-C-エトキシカルポニルニトロンとアルケン類との分子間環化付加反応2009

    • Author(s)
      森田延嘉
    • Organizer
      第39回複素環化学討論会
    • Place of Presentation
      千葉
    • Year and Date
      2009-10-14
    • Related Report
      2009 Annual Research Report
  • [Presentation] 分子内にアレン類を有するニトロンの環化付加反応の開発2009

    • Author(s)
      齋藤由香理
    • Organizer
      第53回日本薬学会関東支部大会
    • Place of Presentation
      埼玉
    • Year and Date
      2009-10-03
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] Intermolecular Cycloaddition of N-Boranonitrone with Alkenes2009

    • Author(s)
      Nobuyoshi Morita
    • Organizer
      16^<th> European Symposium on Organic Chemistry
    • Place of Presentation
      Prague, Czech
    • Year and Date
      2009-07-14
    • Related Report
      2010 Final Research Report
  • [Presentation] Intermolecular Cycloaddition of N-Boranonitrone with Alkenes2009

    • Author(s)
      森田延嘉
    • Organizer
      16^<th> European Symposium on 0rganic Chemistry
    • Place of Presentation
      チェコ
    • Year and Date
      2009-07-14
    • Related Report
      2009 Annual Research Report
  • [Presentation] ニトロンとアレンとの分子内環化付加反応2009

    • Author(s)
      森田延嘉
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-27
    • Related Report
      2010 Final Research Report 2008 Annual Research Report
  • [Presentation] N-ボラノニトロンとアルケン類との分子間環化付加反応2008

    • Author(s)
      森里延嘉
    • Organizer
      第34回反応と合成の進歩シンポジウム
    • Place of Presentation
      京都
    • Year and Date
      2008-11-05
    • Related Report
      2010 Final Research Report
  • [Presentation] N-ボラノニトロンを用いた分子間環化付加反応2008

    • Author(s)
      福井健仁
    • Organizer
      第52回日本薬学会関東支部大会
    • Place of Presentation
      東京
    • Year and Date
      2008-10-04
    • Related Report
      2010 Final Research Report
  • [Presentation] N-ボラノニトロンを用いた分子間環化付加反応2008

    • Author(s)
      福井健仁
    • Organizer
      第52回日本薬学会関東支部大会
    • Place of Presentation
      東京理科大学
    • Year and Date
      2008-10-04
    • Related Report
      2008 Annual Research Report
  • [Presentation] N-ボラノニトロンへのラジカル付加反応の開発2008

    • Author(s)
      福井健仁
    • Organizer
      日本薬学会第128年会
    • Place of Presentation
      横浜
    • Year and Date
      2008-03-27
    • Related Report
      2010 Final Research Report
  • [Presentation] N-ボラノニトロンとアルケン類との分子間環化付加反応の開発2008

    • Author(s)
      森田延嘉
    • Organizer
      第34回反応と合成の進歩シンポジウム
    • Place of Presentation
      京都
    • Related Report
      2008 Annual Research Report
  • [Remarks] ホームページ等

    • URL

      http://www.shoyaku.ac.jp/labosite/yakka/index.html

    • Related Report
      2010 Final Research Report

URL: 

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

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