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Novel Oxidative Synthetic Transformations Driven by Chiral Oxoammmonium Salts

Research Project

Project/Area Number 23659003
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionTohoku University

Principal Investigator

IWABUCHI Yoshiharu  東北大学, 大学院・薬学研究科, 教授 (20211766)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsオキソアンモニウム塩 / アザアダマンタン / 不斉酸化 / アルコール酸化 / 不斉触 媒 / 分子認識 / ニトロキシルラジカル / 酸化反応 / 合成反応 / オキソアンモニウム / 求電子付加 / 精密合成 / 化学選択性 / AZADO
Research Abstract

Novel synthetic use of azaadamantane-type oxoammonium salts has been exploited. It was found that 9-nor-azaadamantane N-oxy (Nor-AZADO) gives the corresponding oxoammonium salts that exhibit superior activities to AZADO derived oxoammonium salts. Several novel oxidative transformations using Nor-AZADO have been developed including (1) silyl enol ethers to a,b-unsaturated ketones and (2) silyl enol ethers to 1,2-diketones.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (13 results)

All 2013 2012 2011 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (5 results) (of which Invited: 2 results) Remarks (2 results)

  • [Journal Article] Oxidation of Nitroxyl Radicals: Electrochemical and Computational Studies2012

    • Author(s)
      Masatoshi Shibuya, Fabio Pichierri, Masaki Tomizawa, Shota Nagasawa, Iwao Suzuki, Yoshiharu Iwabuchi
    • Journal Title

      Tetrahedron Letters

      Volume: 2070-2073 Issue: 16 Pages: 2070-2073

    • DOI

      10.1016/j.tetlet.2012.02.033

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Oxidation of Alcohols to Carbonyl Compounds with Diisopropyl Azodicarboxylate Catalyzed by Nitroxyl Radicals2012

    • Author(s)
      M.Hayashi, M.Shibuya, Y.Iwabuchi
    • Journal Title

      Synlett

      Volume: 23 Issue: 07 Pages: 1025-1030

    • DOI

      10.1055/s-0031-1290528

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Oxidative Conversion of Silyl Enol Ethers to α, β-Unsaturated Ketones Employing Oxoammonium Salts2012

    • Author(s)
      M.Hayashi, M.Shibuya, Y.Iwabuchi
    • Journal Title

      Org.Lett.

      Volume: 14 Issue: 1 Pages: 154-157

    • DOI

      10.1021/ol2029417

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Oxidation of Alcohols to Carbonyl Compounds with Diisopropyl Azodicarboxylate Catalyzed by Nitroxyl Radicals2012

    • Author(s)
      M. Hayashi, M. Shibuya, Y. Iwabuchi
    • Journal Title

      J. Org. Chem

      Volume: 77 Issue: 6 Pages: 3005-3009

    • DOI

      10.1021/jo300088b

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 9-Azanoradamantane N-oxyl (Nor-AZADO): A Highly Active Organocatalyst for Alcohol Oxidation2011

    • Author(s)
      Masaki Hayashi, Yusuke Sasano, Shota Nagasawa, Masatoshi Shibuya, Yoshiharu Iwabuchi
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Pages: 1570-1573

    • NAID

      130001852136

    • URL

      https://www.jstage.jst.go.jp/article/cpb/59/12/59_12_1570/_pdf

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] 9-Azanoradamantane N-oxyl (Nor-AZADO): A Highly Active Organocatalyst for Alcohol Oxidation2011

    • Author(s)
      M. Hayashi, Y. Sasano, S. Nagasawa, M. Shibuya, Y. Iwabuchi
    • Journal Title

      Chem. Pharm. Bull.

      Volume: 59 Pages: 1570-1573

    • NAID

      130001852136

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 新規酸化触媒AZADOの発見と展開2013

    • Author(s)
      岩渕好治
    • Organizer
      日本化学会大93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 高活性アルコール酸化触媒AZADOの開発と天然物合成への活用2012

    • Author(s)
      岩渕好治
    • Organizer
      第54回天然有機化合物討論会
    • Place of Presentation
      東京農業大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] 有機ニトロキシルラジカルを触媒とするアルコール酸化の新展開2012

    • Author(s)
      岩渕好治
    • Organizer
      第45回酸化反応討論会
    • Place of Presentation
      名古屋市立大学
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Highly Active Organocatalyst for Oxidation of Alcohols2011

    • Author(s)
      Masaki Hayashi, Yoshiharu Iwabuchi
    • Organizer
      242nd ACS National Meeting & Exposition
    • Place of Presentation
      Denver (USA)
    • Year and Date
      2011-08-29
    • Related Report
      2012 Final Research Report 2011 Research-status Report
  • [Presentation] キラルAZADO誘導体を触媒とするラセミ第2級アルコールの酸化的速度論的分割法の開発

    • Author(s)
      村上景一
    • Organizer
      第23回万有仙台シンポジウム
    • Place of Presentation
      仙台国際センター
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.pharm.tohoku.ac.jp/~gousei/synthetic/index.html

    • Related Report
      2012 Final Research Report
  • [Remarks] 東北大学大学院薬学研究科 分子制御化学講座 合成制御化学分野HP

    • URL

      http://www.pharm.tohoku.ac.jp/~gousei/gousei-j.shtml

    • Related Report
      2012 Annual Research Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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