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2013 Fiscal Year Final Research Report

Development of novel isocyanide-based reactions

Research Project

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Project/Area Number 24750037
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionKanazawa University

Principal Investigator

SOETA Takahiro  金沢大学, 物質化学系, 助教 (10506819)

Project Period (FY) 2012-04-01 – 2014-03-31
Keywords多成分反応 / イソシアニド / 複素環
Research Abstract

In order to develop a practical method for the construction of crud like and heterocyclic compounds, we have designed a novel Passerini or Ugi reaction system where a compound (which we write in the general form as Z-X) composed of an electrophilic (Z) and nucleophilic (X) could perform the same reactivity as the carboxylic acid. Based on this concept, we have developed the O-silylative Passerini reaction and the borinic acid catalyzed addition of isocyanides to aldehydes. In addition, we have designed and demonstrated the addition reaction of isocyanides to nitrones in the presence of silly halide. Furthermore, a novel [5+1] cycloaddition of isocyanide was explored to afford the hetelocyclic compounds efficiency.

  • Research Products

    (19 results)

All 2014 2013

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (9 results) Book (1 results)

  • [Journal Article] [4+1] Cycloaddition of N-Acyl Imine Derivatives with Isocyanides : Efficient Synthesis of 5-Aminooxazoles and 5-Aminothiazoles2014

    • Author(s)
      Takahiro Soeta, Kaname Tamura, Yutaka Ukaji
    • Journal Title

      Tetrahedron

      Volume: 70 Pages: 3005-3010

    • DOI

      10.1016/j.tet.2014.03.016

    • Peer Reviewed
  • [Journal Article] A One-Pot O-Phosphinative Passerini/Pudovik Reaction : Efficient Synthesis of Highly Functionalizedα-(Phosphinyloxy)amide Derivatives2014

    • Author(s)
      Takahiro Soeta, Syunsuke Matsuzaki, Yutaka Ukaji
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Pages: 5007-5012

    • DOI

      10.1002/chem.201304618

    • Peer Reviewed
  • [Journal Article] Desymmetrization of 1,4-Pentadien-3-ol by the Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines2014

    • Author(s)
      Mari Yoshida, Naotaro Sasa, Tomomitsu Kato, Shuhei Fujinami, Takahiro Soeta, Katsuhiko Inomata, Yutaka Ukaji
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Pages: 2058-2064

    • DOI

      10.1002/chem.201302889

    • Peer Reviewed
  • [Journal Article] Carboxylic Acid Free Novel Isocyanide Based Reaction2014

    • Author(s)
      Takahiro Soeta, Yutaka Ukaji
    • Journal Title

      Chem. Rec.

      Volume: 14 Pages: 101-116

    • DOI

      10.1002/tcr.201300021

    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of (2Z, 4E)-2,4-Pentadien-1-ols via Sequential 1,4-Elimination Reaction and [1,2]-Wittig Rearrangement Starting from (E)-4-Alkoxy-2-butenyl Benzoates2013

    • Author(s)
      Takeo Nakano, Takahiro Soeta, Kohei Endo, Katsuhiko Inomata, Yutaka Ukaji
    • Journal Title

      J. Org. Chem.

      Volume: 78 Pages: 12654-12661

    • DOI

      10.1021/jo402272r

    • Peer Reviewed
  • [Journal Article] Magnesium–Tartramide Complex Mediated Asymmetric Strecker-Type Reaction of Nitrones Using Cyanohydrin2013

    • Author(s)
      Takahiro Sakai, Takahiro Soeta, Kohei Endo, Shuhei Fujinami, Yutaka Ukaji
    • Journal Title

      Org. Lett.

      Volume: 15 Pages: 2422-2425

    • DOI

      10.1021/ol400898p

    • Peer Reviewed
  • [Journal Article] N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Aldehydes with Carbodiimides under Aerobic Conditions : Efficient Synthesis of N-Acylureas2013

    • Author(s)
      Takahiro Soeta, Yuhta Tabatake, Shuhei Fujinami, Yutaka Ukaji
    • Journal Title

      Org. Lett.

      Volume: 15 Pages: 2088-2091

    • DOI

      10.1021/ol400672c

    • Peer Reviewed
  • [Journal Article] Three-Components Reaction of C,N-Cyclic N'-Acyl Azomethine Imines, Isocyanide, and Azide Compounds : Effective Synthesis of 1,5-Disubstituted Tetrazoles Bearing Tetrahydroisoquinoline Skeletons2013

    • Author(s)
      Takahiro Soeta, Kaname Tamura, Shuhei Fujinami, Yutaka Ukaji
    • Journal Title

      Org. Biomol. Chem.

      Volume: 11 Pages: 2168-2174

    • DOI

      10.1039/C3OB27297D

    • Peer Reviewed
  • [Journal Article] One-pot Stereoselective Syntheses of 2-Acylaziridines and 2-Acylpyrrolidines from N-(Propargylic)hydroxylamines2013

    • Author(s)
      Yoshiaki Miyamoto, Norihiro Wada, Takahiro Soeta, Katsuhiko Inomata, Yutaka Ukaji
    • Journal Title

      Chem. Asian J.

      Volume: 8 Pages: 824-831

    • DOI

      10.1002/asia.201201180

    • Peer Reviewed
  • [Presentation] イソシアニドを用いた[4+1]付加環化反応の開発 : ベンゾチオフェン誘導体の高効率的合成2014

    • Author(s)
      奥野巧, 添田貴宏, 宇梶裕
    • Organizer
      日本化学会第94会春季年会
    • Place of Presentation
      名古屋
    • Year and Date
      20140300
  • [Presentation] パラジウム-銅触媒を用いた新規アルコキシカルボニル化反応の開発2014

    • Author(s)
      古屋智樹, 添田貴宏, 遠藤恆平, 宇梶裕
    • Organizer
      日本化学会第94会春季年会
    • Place of Presentation
      名古屋
    • Year and Date
      20140300
  • [Presentation] O-Phosohinative Passerini/Pudovik反応の開発 : α-ヒドロキシホスフィンアミド誘導体の高効率的one-pot合成2014

    • Author(s)
      松崎駿介, 添田貴宏, 宇梶裕
    • Organizer
      日本化学会第94会春季年会
    • Place of Presentation
      名古屋
    • Year and Date
      20140300
  • [Presentation] 含窒素複素環カルベンを用いた新規な有機触媒反応の開発2013

    • Author(s)
      添田貴宏, 田畠雄太, 宇梶裕
    • Organizer
      第104回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      20131100
  • [Presentation] 有機ケイ素化合物を活性化剤とした新規Ugi型反応の開発2013

    • Author(s)
      田村要, 添田貴宏, 宇梶裕
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      岐阜
    • Year and Date
      20131000
  • [Presentation] 新規なイソシアニドの付加-捕捉手法を基盤とする複素環合成反応の開発2013

    • Author(s)
      田村要, 添田貴宏, 宇梶裕
    • Organizer
      平成25年度有機合成化学北陸セミナー
    • Place of Presentation
      金沢
    • Year and Date
      20131000
  • [Presentation] 酒石酸誘導体を不斉源として活用するアゾメチンイミンの不斉1,3-双極子付加環化反応2013

    • Author(s)
      吉田麻里, 佐々直太朗, 加藤智光, 添田貴宏, 猪股勝彦, 宇梶裕
    • Organizer
      平成25年度有機合成化学北陸セミナー
    • Place of Presentation
      金沢
    • Year and Date
      20131000
  • [Presentation] Magnesium-Tartramide Complex Mediated Asymmetric Strecker-Type Reaction of Nitrones Using Cyanohydrin2013

    • Author(s)
      Takahiro Sakai, Takahiro Soeta, Kohei Endo, Shuhei Fujinami, Yutaka Ukaji
    • Organizer
      The 10 th International Symposium on Carbanion Chemistry (ISCC-10)
    • Place of Presentation
      Kyoto
    • Year and Date
      20130900
  • [Presentation] N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Aldehydes with Carbodiimides under Aerobic Conditions : Efficient Synthesis of N-Acylureas2013

    • Author(s)
      Takahiro Soeta, Yuta Tabatake, Yutaka Ukaji
    • Organizer
      1^<st> International Conference & 6^<th> Symposium on Organocatalysis
    • Place of Presentation
      Otsu
    • Year and Date
      20130500
  • [Book] Methods and Applications of Cycloaddition Reactions in Organic Syntheses."Chap.11, Development of New Methods for the Construction of Heterocycles Based on Cycloaddition Reaction of 1,3-Dipoles2014

    • Author(s)
      Yutaka Ukaji, Takahiro Soeta
    • Publisher
      Wiley

URL: 

Published: 2015-06-25  

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