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2008 Fiscal Year Final Research Report

Development of synthetic methods of multisubstituted heterocycliccompounds by catalytic addition of carbon-heteroatom bonds

Research Project

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Project/Area Number 18685011
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionTohoku University

Principal Investigator

NAKAMURA Itaru  Tohoku University, 大学院・理学研究科, 准教授 (00333899)

Project Period (FY) 2006 – 2008
Keywords反応有機化学
Research Abstract

金や白金などのπルイス酸触媒によりインドール、ベンゾフラン、ベンゾチオフェンなどの多置換ヘテロ環を効率的に合成する手法を開発した。特に、炭素官能基のみならず、硫黄やケイ素などのヘテロ原子官能基が転位基として作用することを明らかにした。この研究過程において、O-プロパルギルオキシム化合物が銅触媒により極めて有用性の高い多置換ベータラクタム化合物へと骨格転位する新規反応を見出した。

  • Research Products

    (31 results)

All 2009 2008 2007 2006 Other

All Journal Article (18 results) (of which Peer Reviewed: 18 results) Presentation (11 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Five-Bond Cleavage in Copper-Catalyzed Skeletal Rearrangement of O-Propargyl Arylaldoximes to β-Lactam2009

    • Author(s)
      Itaru Nakamura, Toshiharu Araki, Masahiro Terada
    • Journal Title

      J. Am. Chem. Soc 131

      Pages: 2804-2805

    • Peer Reviewed
  • [Journal Article] Stereochemistry Control by Ester Group or Olefin Ligand in Platinum-Catalyzed Carboalkoxylation of 6-(1-Alkoxyethoxy)hex-2-ynoates2009

    • Author(s)
      Itaru Nakamura, Ching Siew Chan, Toshiharu Araki, Masahiro Terada, Yoshinori Yamamoto
    • Journal Title

      Adv. Synth. Catal 351

      Pages: 1089-1100

    • Peer Reviewed
  • [Journal Article] Platinum-Catalyzed Consecutive C-N bond Formation-[1, 3] Shift of Carbamoyl and Ester Groups2009

    • Author(s)
      Itaru Nakamura, Yusuke Sato, Sayaka Konta, Masahiro Terada
    • Journal Title

      Tetrahedron Letters 50

      Pages: 2075-2077

    • Peer Reviewed
  • [Journal Article] Platinum-Catalyzed Dehydroalkoxylation-Cyclization Cascade via N-O Bond Cleavage2009

    • Author(s)
      Itaru Nakamura, Yusuke Sato, Masahiro Terada
    • Journal Title

      J. Am. Chem. Soc 131

      Pages: 4198-4199

    • Peer Reviewed
  • [Journal Article] Pt-Catalyzed Multi-Substituted Benzo[b]selenophene2009

    • Author(s)
      Takuma Sato, Itaru Nakamura, Masahiro Terada
    • Journal Title

      Eur. J. Org. Chem

      Pages: 5509

    • Peer Reviewed
  • [Journal Article] Gold-catalyzed consecutive [1, 2] alkyl migration-oxygen transfer reaction of 2-alkynyl-1-tetralones2009

    • Author(s)
      Ching Siew Chan, Toshiharu Araki, Itaru Nakamura, Masahiro Terada
    • Journal Title

      Tetrahedron Lett 50

      Pages: 216-218

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Indolization of N-Aroylbenzotriazoles with Disubstituted Alkynes2009

    • Author(s)
      Itaru Nakamura, Tetsuya Nemoto, Naozumi Shiraiwa, Masahiro Terada
    • Journal Title

      Org. Lett 11

      Pages: 1055-1058

    • Peer Reviewed
  • [Journal Article] Synthesis of Multisubstituted 2-(Dihydrofuran-2(3H) -ylidene)acetates via Intramolecular Carboalkoxylation by Platinum-Olefin Catalyst System2008

    • Author(s)
      Itaru Nakamura, Ching Siew Chan, Toshiharu Araki, Masahiro Terada, Yoshinori Yamamoto
    • Journal Title

      Org. Lett 10

      Pages: 309-312

    • Peer Reviewed
  • [Journal Article] Chirality Transfer in Gold-Catalyzed Carbothiolation of ortho-Alkynylphenyl 1-Arylethyl Sulfides2008

    • Author(s)
      Itaru Nakamura, Takuma Sato, Masahiro Terada, Yoshinori Yamamoto
    • Journal Title

      Org. Lett 10

      Pages: 2649-2651

    • Peer Reviewed
  • [Journal Article] Synthesis of 3- and 6-Sulfonylindoles from ortho-Alkynyl-N-sulfonylanilines by the Use of Lewis Acidic Transition Metal Catalysts2008

    • Author(s)
      Itaru Nakamura, Uichiro Yamagishi, Dschun Song, Sayaka Konta, Yoshinori Yamamoto
    • Journal Title

      Chem. Asian J 3

      Pages: 285-295

    • Peer Reviewed
  • [Journal Article] Gold- and Indium-Catalyzed Synthesis of 3- and 6-Sulofonylindoles from ortho-Alkynyl-N-Sulufonylanilines. Consecutive C-N and C-S Bond Formation through Intramolecular Aminosulfonylation2007

    • Author(s)
      Itaru Nakamura, Uichiro Yamagishi, Dschun Song, Sayaka Konta, Yoshinori Yamamoto
    • Journal Title

      Angew. Chem. Int. Ed 46

      Pages: 2284-2287

    • Peer Reviewed
  • [Journal Article] Gold-catalyzed cyclization of (ortho-alkynylphenylthio)silanes; intramolecular capture of the vinyl-Au intermediate by the silicon electrophile2007

    • Author(s)
      Itaru Nakamura, Takuma Sato, Masahiro Terada, Yoshinori Yamamoto
    • Journal Title

      Org. Lett 9

      Pages: 4081-4083

    • Peer Reviewed
  • [Journal Article] Synthesis of 1, 2, 3, 4-Tetrasubstituted Pyrroles Derivatives via the Palladium-Catalyzed Reaction of 1, 3-Diketones with Methyleneaziridines2007

    • Author(s)
      Kalum K.A.D.S. Kathriarachchi, Amal I. Siriwardana, Itaru Nakamura, Yoshinori Yamamoto
    • Journal Title

      Tetrahedron Lett 48

      Pages: 2267-2270

    • Peer Reviewed
  • [Journal Article] Synthesis of 2, 3-disubstituted benzofurans and indoles byπ-Lewis acidic transition metal-catalyzed cyclization of ortho-alkynylphenyl O, O- and N, O-acetals2007

    • Author(s)
      Itaru Nakamura, Yuya Mizushima, Uichiro Yamagishi, Yoshinori Yamamoto
    • Journal Title

      Tetrahedron 63

      Pages: 8670-8676

    • Peer Reviewed
  • [Journal Article] Thermally Induced [2+2] Cycloadditions of (Benzyloxymethylene)cyclopropane to Alkylidenemalononitriles2007

    • Author(s)
      Itaru Nakamura, Ryoko Nagata, Tetsuya Nemoto, Masahiro Terada, Yoshinori Yamamoto, Thomas Spath, Armin de Meijere
    • Journal Title

      Eur. J. Org. Chem

      Pages: 4479-4482

    • Peer Reviewed
  • [Journal Article] Gold-Catalyzed Intramolecular Carbothiolation of Alkynes. Synthesis of 2, 3-Disubstituted Benzothiophenes fromα-Alkoxylalkyl (ortho-Alkynyl)phenyl Sulfides2006

    • Author(s)
      Itaru Nakamura, Takuma Sato, Yoshinori Yamamoto
    • Journal Title

      Angew. Chem. Int. Ed 45

      Pages: 4473-4475

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Dimerization of Conjugated Diynes: Synthesis of (E)-1, 2-Divinyldiethynylethenes Having Donor and Acceptor Chromophores at the Terminus of Alkyne2006

    • Author(s)
      Nirmal K. Pahadi, Draxel H. Camacho, Itaru Nakamura, Yoshinori Yamamoto
    • Journal Title

      J. Org. Chem 71(3)

      Pages: 1152-1155

    • Peer Reviewed
  • [Journal Article] Thermally Induced and Silver Salt-Catalyzed [2+2] Cycloadditions of Imines to (Alkoxymethylene)cyclopropanes2006

    • Author(s)
      Itaru Nakamura, Tetsuya Nemoto, Yoshinori Yamamoto, Armin de Meijere
    • Journal Title

      Angew. Chem. Int. Ed 45

      Pages: 5176-5179

    • Peer Reviewed
  • [Presentation] 白金触媒によるN-O結合の開裂を伴う脱アルコール環化反応2009

    • Author(s)
      中村達・佐藤悠介・寺田眞浩
    • Organizer
      第39回複素環化学討論会
    • Place of Presentation
      柏
    • Year and Date
      20091014-20091016
  • [Presentation] 銅触媒による5つの結合の開裂を伴う新規骨格転位反応2009

    • Author(s)
      中村達・新木利治・寺田眞浩
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都
    • Year and Date
      20090909-20090911
  • [Presentation] n-o結合の開裂を経由する新規π酸性遷移金属触媒反応2009

    • Author(s)
      中村達
    • Organizer
      平成21年度化学系学協会東北大会
    • Place of Presentation
      郡山
    • Year and Date
      20090909-20090911
  • [Presentation] N-O結合の開裂を経由する新規π酸性遷移金属触媒反応2009

    • Author(s)
      中村達
    • Organizer
      京都大学グローバルcoe有機若手ワークショップ
    • Place of Presentation
      京都
    • Year and Date
      20090907-20090908
  • [Presentation] Five-Bond Cleavage in Copper-Catalyzed Skeletal Rearrangement of O-Propargyl Arylaldoximes to β-Lactams2009

    • Author(s)
      Itaru Nakamura, Toshiharu Araki, Masahiro Terada
    • Organizer
      15th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 15)
    • Place of Presentation
      Glasgow, Switzerland
    • Year and Date
      20090726-20090730
  • [Presentation] 5つの結合の開裂を伴う触媒的骨格転位反応2009

    • Author(s)
      中村達・新木利治・寺田眞浩
    • Organizer
      第95回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      20090610-20090911
  • [Presentation] 金属触媒を用いた新規医薬(中間体)の合成技術」2009

    • Author(s)
      中村達
    • Organizer
      矢野経済研究所"東北テクノアーチ特許技術ご紹介セミナー第1弾「医療・ライフサイエンスの未来」
    • Place of Presentation
      東京
    • Year and Date
      2009-12-02
  • [Presentation] π酸性遷移金属触媒による多置換ヘテロ環構築反応の開発2009

    • Author(s)
      中村達
    • Organizer
      有機金属若手研究者の会
    • Place of Presentation
      京都
    • Year and Date
      2009-09-08
  • [Presentation] 白金-オレフィン触媒系による分子内カルボアルコキシ化反応2007

    • Author(s)
      中村達・水島祐也・Ching Siew Chan・新木利治・寺田眞浩・山本嘉則
    • Organizer
      第100回触媒討論会
    • Place of Presentation
      札幌
    • Year and Date
      20070917-20070920
  • [Presentation] Synthesis of Multi-substituted Heteroarenes via Catalytic Carbon-Heteroatom Bond Addition2006

    • Author(s)
      Nakamura, I.; Mizushima, Y.; Yamagishi, U.; Sato, T.; Song, D.; Konta, S.; Terada, M.; Yamamoto, Y
    • Organizer
      The Tenth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-10)
    • Place of Presentation
      Kyoto
    • Year and Date
      20061113-20061117
  • [Presentation] 炭素-ヘテロ原子結合の触媒的付加反応による多置換複素芳香環化合物の合成2006

    • Author(s)
      中村達・水島祐也・嶋田朋嘉・山岸宇一郎・佐藤太久真・ソンジュン・今田さやか・寺田眞浩・山本嘉則
    • Organizer
      第53回有機金属化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      20060908-20060909
  • [Remarks]

    • URL

      http://www.orgreact.sakura.ne.jp/index.html

  • [Patent(Industrial Property Rights)] 新規β-ラクタム合成法2009

    • Inventor(s)
      中村達、寺田眞浩、新木利治
    • Industrial Property Rights Holder
      東北大学
    • Industrial Property Number
      出願特願2009-191400
    • Filing Date
      2009-08-04

URL: 

Published: 2011-06-18   Modified: 2016-04-21  

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