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2012 Fiscal Year Final Research Report

Novel Oxidative Synthetic Transformations Driven by Chiral Oxoammmonium Salts

Research Project

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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
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
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.

  • Research Products

    (6 results)

All 2012 2011 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (1 results) Remarks (1 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

    • DOI

      DOI:10.1016/j.tetlet.2012.02.033

    • Peer Reviewed
  • [Journal Article] Oxidation of Alcohols to Carbonyl Compounds with Diisopropyl Azodicarboxylate Catalyzed by Nitroxyl Radicals2012

    • Author(s)
      Masaki Hayashi, Masatoshi Shibuya, Yoshiharu Iwabuchi
    • Journal Title

      Synlett

      Volume: 23 Pages: 1025-1030

    • DOI

      DOI:10.1055/s-0031-1290528

    • Peer Reviewed
  • [Journal Article] Oxidative Conversion of Silyl Enol Ethers to α,β-Unsaturated Ketones Employing Oxoammonium Salts2012

    • Author(s)
      Masaki Hayashi, Masatoshi Shibuya, Yoshiharu Iwabuchi
    • Journal Title

      Organic Letters

      Volume: 14 Pages: 154-157

    • DOI

      DOI:10.1021/ol2029417

    • 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

    • URL

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

    • Peer Reviewed
  • [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
  • [Remarks]

    • URL

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

URL: 

Published: 2014-09-25  

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