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Chemoselective aerobic oxidation of amino alcohols using nitroxyl radical-copper catalysis

Research Project

Project/Area Number 25860001
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

SASANO Yusuke  東北大学, 薬学研究科(研究院), 助教 (10636400)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsアルコール酸化反応 / 酸化的速度論的光学分割 / アミノアルコール / ニトロキシルラジカル / 銅 / キラルオキサゾリン
Outline of Final Research Achievements

Highly chemoslective aerobic alcohol oxidation using nitroxyl radical-copper catalysis has been developed. During close optimization of the reaction conditions by using various alcohols, we found that the optimum combination of nitroxyl radical, copper salt, and solution concentration was dependent on the type of substrate. Various alcohols, including amino alcohols, were efficiently oxidized into their corresponding carbonyl compounds under mild conditions with lower amounts of the catalysts.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (8 results)

All 2015 2014 2013

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

  • [Journal Article] Highly Efficient Aerobic Oxidation of Alcohols by Using Less-Hindered Nitroxyl-Radical/Copper Catalysis: Optimum Catalyst Combinations and Their Substrate Scope2015

    • Author(s)
      Sasano, Y.; Kogure, N.; Nishiyama, T.; Nagasawa, S.; Iwabuchi, Y.
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 10 Issue: 4 Pages: 1004-1009

    • DOI

      10.1002/asia.201403245

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Chemoselective Aerobic Oxidation of Amino Alcohols into Amino Carbonyl Compounds2014

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

      Angewandte Chemie International Edition

      Volume: 53 Issue: 12 Pages: 3236-3240

    • DOI

      10.1002/anie.201309634

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 有機ニトロキシルラジカル-銅触媒系を用いたアルコール空気酸化反応条件の最適化2015

    • Author(s)
      小暮直貴,笹野裕介,西山智弘,長澤翔太,岩渕好治
    • Organizer
      日本薬学会 第135年会
    • Place of Presentation
      神戸市
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] AZADO-銅触媒系によるアミノアルコール類の高化学選択的空気酸化反応の開発と応用2014

    • Author(s)
      長澤翔太,笹野裕介,澁谷正俊,Jaiwook Park,岩渕好治
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      東北大学川内萩ホール(仙台市)
    • Year and Date
      2014-11-10 – 2014-11-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] AZADO-銅触媒系を用いたアミノアルコール類の高化学選択的空気酸化反応2014

    • Author(s)
      長澤翔太,笹野裕介,澁谷正俊,岩渕好治
    • Organizer
      第25回記念万有仙台シンポジウム
    • Place of Presentation
      仙台国際センター(仙台市)
    • Year and Date
      2014-06-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] AZADO-銅協奏型触媒を用いたアルコール類の空気酸化反応2013

    • Author(s)
      西山智弘,笹野裕介,長澤翔太,岩渕好治
    • Organizer
      第52回日本薬学会東北支部大会
    • Place of Presentation
      東北大学(仙台市)
    • Related Report
      2013 Research-status Report
  • [Presentation] AZADOを触媒とするアルコール類の高効率的空気酸化反応の開発と応用2013

    • Author(s)
      長澤翔太,長田祐二,西山智弘,笹野裕介,澁谷正俊,岩渕好治
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      タワーホール船堀 (東京都)
    • Related Report
      2013 Research-status Report
  • [Presentation] AZADO-銅触媒系を用いるアミノアルコール類の高化学選択的空気酸化反応2013

    • Author(s)
      長澤翔太,笹野裕介,西山智弘,澁谷正俊,岩渕好治
    • Organizer
      第46回酸化反応討論会
    • Place of Presentation
      筑波大学(つくば市)
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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