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Exploitation of the unique reactivity of diazocarbonyl compounds for the development of practical synthetic methods

Research Project

Project/Area Number 21750041
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionKyoto University

Principal Investigator

HASHIMOTO Takuya  Kyoto University, 大学院・理学研究科, 助教 (20437198)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsジアゾ化合物 / 酸触媒 / 触媒的不斉合成 / キラルブレンステッド酸 / キラルルイス酸 / アジリジン / 不斉補助基 / 不斉合成
Research Abstract

This research project was aimed at the development of novel synthetic methods based on the use of α-diazocarbonyl compounds, as it was anticipated to reveal straightforward ways for the preparation of complex molecules. This study led to the finding of novel synthetic methods for valuable synthetic building blocks, such as seven-membered carbocycles, β-keto carbonyl compounds and aziridines, which are commonly seen in anticancer drugs and other biologically active materials.

Report

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

    (29 results)

All 2011 2010 2009 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (16 results) Remarks (1 results)

  • [Journal Article] Development of a Practical Synthetic Method for N-tert-Butoxycarbonyl α-Ketimino Esters.2011

    • Author(s)
      Hashimoto, T, Yamamoto, K.Maruoka, K.
    • Journal Title

      Chem.Lett. 40

      Pages: 326-327

    • NAID

      10027816144

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric trisubstituted aziridination of aldimines and ketimines using N-α-diazoacyl camphorsultams.2011

    • Author(s)
      Hashimoto, T, Nakatsu, H, Yamamoto, K, Watanabe, S, Maruoka, K.
    • Journal Title

      Chem.Asian J. 6

      Pages: 607-613

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Development of a practical synthetic method for N-tert-butoxycarbonyl α-ketimino esters2011

    • Author(s)
      Hashimoto, T., Yamamoto, K.Maruoka, K.
    • Journal Title

      Chemistry Letters

      Volume: 40 Pages: 326-327

    • NAID

      10027816144

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric trisubstituted aziridination of aldimines and ketimines using N-α-diazoacyl camphorsultams2011

    • Author(s)
      Hashimoto, T., Nakatsu, H., Yamamoto, K., Watanabe, S., Maruoka, K.
    • Journal Title

      Chemistry-an Asian Journal

      Volume: 6 Pages: 607-613

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Desymmetrizing asymmetric ring expansion : Stereoselective synthesis of 7-membered cyclic SS-keto carbonyl compounds with an α-hydrogen.2010

    • Author(s)
      Hashimoto, T, Naganawa, Y, Maruoka, K.
    • Journal Title

      Chem.Commun. 46

      Pages: 6810-6812

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of trisubstituted aziridines with N-α-diazoacyl camphorsultam.2010

    • Author(s)
      Hashimoto, T, Nakatsu, H, Watanabe, S. Maruoka, K.
    • Journal Title

      Org.Lett. 12

      Pages: 1668-1671

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Desymmetrizing asymmetric ring expansion : Stereoselective synthesis of 7-membered cyclic β-keto carbonyl compounds with an α-hydrogen2010

    • Author(s)
      Hashimoto, T., Naganawa, Y., Maruoka, K.
    • Journal Title

      Chemical Communications

      Volume: 46 Pages: 6810-6812

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of Trisubstituted Aziridines with N-α-Diazoacyl Camphorsultam2010

    • Author(s)
      Takuya Hashimoto, Hiroki Nakatsu, Shogo Watanabe, Keiji Maruoka
    • Journal Title

      Organic Letters 12

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of α-alkyl-SS-keto imides via asymmetric redox C-C bond formation between α-alkyl-α-diazocarbonyl compounds and aldehydes.2009

    • Author(s)
      Hashimoto, T, Miyamoto, H, Naganawa, Y, Maruoka, K.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 11280-11281

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective construction of seven-membered rings with an all-carbon quaternary center by direct Tiffeneau-Demjanov-type ring expansion.2009

    • Author(s)
      Hashimoto, T, Naganawa, Y. Maruoka, K.
    • Journal Title

      J.Am.Chem.Soc 131

      Pages: 6614-6617

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau-Demjanov-type Ring Expansion2009

    • Author(s)
      Takuya Hashimoto, Yuki Naganawa, Keiji Maruoka
    • Journal Title

      Journal of the American Chemical Society 131

      Pages: 6614-6617

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of α-Alkyl-β-keto Imides via Asymmetric Redox C-C Bond Formation between α-Alkyl-α-diazocarbonyl Compounds and Aldehydes2009

    • Author(s)
      Takuya Hashimoto, Hisashi Miyamoto, Yuki Naganawa, Keiji Maruoka
    • Journal Title

      Journal of the American Chemical Society 131

      Pages: 11280-11281

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] N-Boc保護ケチミノエステルの新規合成法の開発と三置換アジリジン化反応への応用2011

    • Author(s)
      山本久美子、橋本卓也、丸岡啓二
    • Organizer
      日本化学会91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] キラルブレンステッド酸を用いた触媒的不斉三置換アジリジン合成法の開発2011

    • Author(s)
      中津大貴、橋本卓也、丸岡啓二
    • Organizer
      日本化学会91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] キラルアルミニウムルイス酸触媒を用いた立体選択的環拡大反応の開発2011

    • Author(s)
      永縄友規、橋本卓也、丸岡啓二
    • Organizer
      日本化学会91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] ジアゾカルボニル化合物を利用した酸触媒反応の展開2011

    • Author(s)
      橋本卓也
    • Organizer
      日本化学会91春季年会若い世代の特別講演
    • Place of Presentation
      神奈川大学(神奈川)(招待講演)
    • Year and Date
      2011-03-28
    • Related Report
      2010 Annual Research Report
  • [Presentation] (A講演)N-Boc保護ケチミノエステルの新規合成法の開発と三置換アジリジン化反応への応用2011

    • Author(s)
      山本久美子、橋本卓也、丸岡啓二
    • Organizer
      日本化学会91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Related Report
      2010 Final Research Report
  • [Presentation] (A講演)キラルブレンステッド酸を用いた触媒的不斉三置換アジリジン合成法の開発2011

    • Author(s)
      中津大貴、橋本卓也、丸岡啓二
    • Organizer
      日本化学会91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Related Report
      2010 Final Research Report
  • [Presentation] (A講演)キラルアルミニウムルイス酸触媒を用いた立体選択的環拡大反応の開発2011

    • Author(s)
      永縄友規、橋本卓也、丸岡啓二
    • Organizer
      日本化学会91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Related Report
      2010 Final Research Report
  • [Presentation] (若い世代の特別講演)ジアゾカルボニル化合物を利用した酸触媒反応の展開2011

    • Author(s)
      橋本卓也
    • Organizer
      日本化学会91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Related Report
      2010 Final Research Report
  • [Presentation] N-α-ジアゾアシルカンファーサルタムを用いた不斉三置換アジリジン化反応の開発2010

    • Author(s)
      中津大貴、渡邊将吾、橋本卓也、丸岡啓一
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 環拡大を利用したα-水素を持つ環状β-ケトカルボニル化合物の立体選択的構築2010

    • Author(s)
      永縄友規、橋本卓也、丸岡啓二
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 環拡大を利用したα-水素を持つ環状SS-ケトカルボニル化合物の立体選択的構築(A講演)2010

    • Author(s)
      永縄友規、橋本卓也、丸岡啓二
    • Organizer
      日本化学会90春季年会
    • Place of Presentation
      近畿大学(大阪)
    • Related Report
      2010 Final Research Report
  • [Presentation] N-α-ジアゾアシルカンファーサルタムを用いた不斉三置換アジリジン化反応の開発(A講演)2010

    • Author(s)
      中津大貴、橋本卓也、丸岡啓二
    • Organizer
      日本化学会90春季年会
    • Place of Presentation
      近畿大学(大阪)
    • Related Report
      2010 Final Research Report
  • [Presentation] New Aspects of Acid-catalyzed reactions using α-diazocarbonyl compound2010

    • Author(s)
      Takuya Hashimoto, Keiji Maruoka
    • Organizer
      Chirality 2010
    • Place of Presentation
      Sapporo Convention center(Hokkaido)
    • Related Report
      2010 Annual Research Report
  • [Presentation] 直截的Tiffeneau-Demjanov型環拡大反応による高立体選択的七員環骨格の構築2010

    • Author(s)
      永縄友規、橋本卓也、丸岡啓二
    • Organizer
      第27回有機合成化学セミナー
    • Place of Presentation
      舞子ビラ神戸(兵庫)
    • Related Report
      2010 Annual Research Report
  • [Presentation] Stereoselective synthesis of trisubstituted aziridines with N-α-diazoacyl camphorsultam2010

    • Author(s)
      Hiroki Nakatsu, Takuya Hashimoto, Keiji Maruoka
    • Organizer
      PACIFICHEM 2010
    • Place of Presentation
      Kamehameha Halls II and III (Honolulu) USA
    • Related Report
      2010 Annual Research Report
  • [Presentation] Stereoselective construction of seven-membered rings with an all-carbon quaternary center by direct Tiffeneau-Demjanov-type ring expansion2010

    • Author(s)
      Yuki Naganawa, Takuya Hashimoto, Keiji Maruoka
    • Organizer
      PACIFICHEM 2010
    • Place of Presentation
      Kamehameha Halls II and III (Honolulu) USA
    • Related Report
      2010 Annual Research Report
  • [Remarks] ホームページ

    • URL

      http://kuchem.kyoto-u.ac.jp/yugo/index.html

    • Related Report
      2010 Final Research Report

URL: 

Published: 2009-04-01   Modified: 2016-04-21  

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