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2012 Fiscal Year Final Research Report

Development of Novel Carbon-Carbon Bond Forming Reactions for Application to Industrial Process

Research Project

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Project/Area Number 23750104
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

AIKAWA Kousuke  東京工業大学, 大学院・理工学研究科, 助教 (30401532)

Project Period (FY) 2011 – 2012
Keywords不斉合成 / 反応 / 炭素-炭素結合生成反応
Research Abstract

I have succeeded in highly enantioselective and atom-economical reactions, especially [2 + 2] cycloaddition of diverse array of alkynes with trifluoropyruvate using chiral dicationic BINAP-Pd catalyst to provide the unprecedentedly stable oxetene derivatives. The reaction takes place with good-to-excellent yields and various substituents on the internal alkynes. This catalytic process offers not only the first synthetic method of stable oxetene derivatives but also new entry to oxetenes as a novel chiral trifluoromethyl building block for pharmaceuticals and agrochemicals.

  • Research Products

    (16 results)

All 2013 2012 2011 Other

All Journal Article (6 results) (of which Peer Reviewed: 4 results) Presentation (9 results) Remarks (1 results)

  • [Journal Article] Development of Catalytic Asymmetric Reactions Based on Chirally Flexible (Tropos) Ligands2012

    • Author(s)
      Kohsuke Aikawa, Koichi Mikami
    • Journal Title

      J. Synth. Org. Chem., Jpn. (Yuki Gosei KagakuKyokaishi)

      Volume: 70 (1) Pages: 45-58

    • Peer Reviewed
  • [Journal Article] Asymmetric Catalysis based on Tropos Ligands2012

    • Author(s)
      Kohsuke Aikawa, Koichi Mikami
    • Journal Title

      Chem. Commun

      Volume: 48 (90) Pages: 11050-11069

    • Peer Reviewed
  • [Journal Article] Stable Axial Chirality in Metal Complexes Bearing4,4'-Substituted BIPHEPs: Application to Catalytic Asymmetric Carbon-Carbon Bond-Forming Reactions2012

    • Author(s)
      Kohsuke Aikawa, Yoshitaka Miyazaki, Koichi Mikami
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 85 (2) Pages: 201-208

    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis of StableOxetenes via Lewis Acid-promoted [2+2] Cycloaddition2011

    • Author(s)
      Kohsuke Aikawa, Yuta Hioki, Natsumi Shimizu, Koichi Mikami
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 133 (50) Pages: 20092-20095

    • Peer Reviewed
  • [Journal Article] Fragment-Based Reaction Discovery of Non-Ene-Type Carbon-Carbon Bond-Forming Reactions: Catalytic Asymmetric Oxetane Synthesis by Screening Olefinic Reactants without Allylic Hydrogen2011

    • Author(s)
      Koichi Mikami, Kohsuke Aikawa, Junpei Aida
    • Journal Title

      Synlett

      Volume: 18 Pages: 2719-2724

  • [Journal Article] Highly enantioselective Friedel-Crafts alkylation of indole and pyrrole with β,γ-unsaturated α-ketoester catalyzed by chiral dicationic palladium complex2011

    • Author(s)
      Kohsuke Aikawa, Kazuya Honda, Shunsuke Mimura, Koichi Mikami
    • Journal Title

      Tetrahedron Lett.

      Volume: 52 (50) Pages: 6682-6686

  • [Presentation] カチオン性キラルパラジウム触媒を用いた不斉ヘテロアリール化反応の開発と連続反応への展開2013

    • Author(s)
      浅井裕也、日置優太、相川光介、三上幸一
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学草津キャンパス
    • Year and Date
      2013-03-23
  • [Presentation] オキセテンの熱的開環反応によるトリフルオロメチル基を有する四置換オレフィンの立体選択的合成とその合成的応用2013

    • Author(s)
      清水なつみ、日置優太、相川光介、三上幸一
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学草津キャンパス
    • Year and Date
      2013-03-22
  • [Presentation] カチオン性パラジウム錯体を用いた触媒的不斉合成2013

    • Author(s)
      相川光介
    • Organizer
      日本化学会第93春季年会(若い世代の特別講演会)
    • Place of Presentation
      立命館大学草津キャンパス
    • Year and Date
      2013-03-22
  • [Presentation] アセチレン化合物を求核剤とする触媒的不斉炭素-炭素結合生成反応の開発2012

    • Author(s)
      清水なつみ、相川光介、三上幸一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2012-03-25
  • [Presentation] カチオン性キラルパラジウム触媒を用いた不斉Diels-Alder反応の開発及びその選択性に関する計算化学的分析2012

    • Author(s)
      本田和也、相川光介、三上幸一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2012-03-25
  • [Presentation] アセチレン化合物を求核剤とする触媒的不斉炭素-炭素結合生成反応の開発2011

    • Author(s)
      清水なつみ、相川光介、三上幸一
    • Organizer
      第28回有機合成セミナー
    • Place of Presentation
      滝の湯(山形県)
    • Year and Date
      20110831-0902
  • [Presentation] カチオン性キラルPd触媒を用いたアルキンを求電子剤とするDiels-Alder反応の開発2011

    • Author(s)
      本田和也、相川光介、三上幸一
    • Organizer
      第28回有機合成セミナー
    • Place of Presentation
      滝の湯(山形県)
    • Year and Date
      20110831-0902
  • [Presentation] ジカチオン性パラジウム触媒を用いた不斉炭素-炭素結合生成反応の開発2011

    • Author(s)
      相川光介
    • Organizer
      有機合成化学協会関東支部平成23年度若手研究者のためのセミナー
    • Place of Presentation
      東京農工大学
    • Year and Date
      2011-10-22
  • [Presentation] 触媒的不斉炭素-炭素生成反応による光学活性含CF3化合物の効率的合成法2011

    • Author(s)
      相川光介、日置優太、清水なつみ、三上幸一
    • Organizer
      第35回フッ素化学討論会
    • Year and Date
      2011-09-27
  • [Remarks]

    • URL

      http://www.apc.titech.ac.jp/~mikami/index-j.html

URL: 

Published: 2014-09-25  

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