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Multi-component coupling reactions based on the additions of cation pools to carbon-carbon multiple bonds

Research Project

Project/Area Number 18350020
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOkayama University (2008)
Kyoto University (2006-2007)

Principal Investigator

SUGA Seiji  Okayama University, 大学院・自然科学研究科, 教授 (50291430)

Project Period (FY) 2006 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥16,060,000 (Direct Cost: ¥14,800,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2008: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2007: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2006: ¥10,600,000 (Direct Cost: ¥10,600,000)
Keywords炭素カチオン / 多成分反応 / 有機電子移動反応 / カチオンプール法 / 立体選択的 / 三成分反応 / エナミン / N-アシルイミニウムイオン / 炭素-炭素多重結合 / マイクロ反応システム / アルケン / テトラヒドロフラン環 / 環化反応 / 立体選択的反応 / γ-ラクトン / N-アシルイミニウムイン / endo / exo選択性
Research Abstract

Multi-component coupling reactions, especially three-component reactions based on the sequential additions of nucleophiles and electrophiles to carbon-carbon multiple bonds are quite important to provide a variety of organic compounds ; however, there are few examples of the reactions initiated by the additions of carbocations to carbon-carbon multiple bonds. In this project, we focus on the development of this type of cationic multi-component couplings on the basis of the cattion pool method. We have developed a new method to construct a substituted tetrahydrofuran ring in a highly stereoselective manner by using intramolecular cationic carbo-hydroxylation, and a method to provide chiral diamino alcohols which is based on the sequential C-C bond formations initiated by the addition of a cation pool to an enamide.

Report

(4 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • 2006 Annual Research Report
  • Research Products

    (59 results)

All 2010 2009 2008 2007 2006

All Journal Article (23 results) (of which Peer Reviewed: 8 results) Presentation (35 results) Book (1 results)

  • [Journal Article] Cationic Three-component Coupling Involving an Optically Active Enamine Derivative. From Time Integration to Space Integration of Reactions2010

    • Author(s)
      Suga, S. ; Yamada, D.
    • Journal Title

      Yoshida, J. Chem. Lett. 39

      Pages: 404-406

    • NAID

      10027179672

    • Related Report
      2008 Final Research Report
  • [Journal Article] Addition of ArSSAr to Carbon-Carbon Multiple Bonds Using Electrochemistry2010

    • Author(s)
      Fujie, S. ; Matsumoto, K. ; Suga, S. ; Nokami, T. ; Yoshida
    • Journal Title

      J. Tetrahedron 66

      Pages: 2823-2829

    • NAID

      120002141660

    • Related Report
      2008 Final Research Report
  • [Journal Article] Addition of ArSSAr to Dienes via Intramolecular C-C Bond Formation Initiated by a Catalytic Amount of ArS+. Matsumoto2009

    • Author(s)
      K. ; Fujie, S. ; Suga, S. ; Nokami, T. ; Yoshida
    • Journal Title

      J. Chem. Commun.

      Pages: 5448-5450

    • Related Report
      2008 Final Research Report
  • [Journal Article] Direct and Indirect Electrochemical Generation of Alkoxycarbenium Ion Pools from Thioacetals.2009

    • Author(s)
      Matsumoto, K. ; Ueoka, K. ; Suzuki, S. ; Suga, S. ; Yoshida
    • Journal Title

      J. Tetrahedron 65

      Pages: 10901-10907

    • NAID

      120001750035

    • Related Report
      2008 Final Research Report
  • [Journal Article] Thiofluorination of Carbon-Carbon Multiple Bonds Using Electrochemically Generated ArS(ArSSAr)+ BF4-2009

    • Author(s)
      Fujie, S. ; Matsumoto, K. ; Suga, S. ; Yoshida
    • Journal Title

      J. Chem. Lett. 38

      Pages: 1186-1187

    • NAID

      130004425418

    • Related Report
      2008 Final Research Report
  • [Journal Article] Synthesis of Thiochromans Based on Indirect Cation Pool Method.2008

    • Author(s)
      Matsumoto, K. ; Ueoka, K. ; Fujie, S. ; Suga, S. ; Yoshida
    • Journal Title

      J. Heterocycles 76

      Pages: 1103-1119

    • Related Report
      2008 Final Research Report
  • [Journal Article] Microflow System Controlled Carbocationic Polymerization of Vinyl Ethers2008

    • Author(s)
      Nagaki, A. ; Iwasaki, T. ; Kawamura, K. ; Yamada, D. ; Suga, S. ; Ando, T. ; Sawamoto, M. ; Yoshida
    • Journal Title

      J. Chem. Asian. J. 3

      Pages: 1558-1567

    • Related Report
      2008 Final Research Report
  • [Journal Article] An Electroinitiated Cation Chain Reaction: Intramolecular Carbon-Carbon Bond Formation Between Thioacetal and Olefin Groups2008

    • Author(s)
      Matsumoto, K. ; Fujie, S. ; Ueoka, K. ; Suga, S. ; Yoshida
    • Journal Title

      J. Angew. Chem. Int. Ed. 47

      Pages: 2506-2508

    • Related Report
      2008 Final Research Report
  • [Journal Article] An Electroinitiated Cation Chain Reaction : Intramolecular Carbon-Carbon Bond Formation Between Thioacetal and Olefin Groups2008

    • Author(s)
      Matsumoto, K.; Fujie, S.; Ueoka, K.; Suga, S.; Yoshida J
    • Journal Title

      Angew.Chem.Int.Ed. 47

      Pages: 2506-2508

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iterative Molecular Assembly Based on the Cation-Pool method. Convergent Synthesis of Dendritic Molecules2008

    • Author(s)
      Nokami, T.; Ohata, K.; Inoue, M.; Tsuyama, H.Shibuya, A.; Soga, K.; Okajima, M.; Suga, S.; Yoshida, J.
    • Journal Title

      J.Am.Chem.Soc. 130

      Pages: 10864-10865

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electro-initiated Coupling Reactions of N-Acyliminium Ion Pools with Arylthiomethylsilanes and Aryloxymethylsilanes2008

    • Author(s)
      Suga, S.; Shimizu, I.; Ashikari, Y.; Mizuno, Y.; Maruyama, T.; Yoshida, J.
    • Journal Title

      Chem.Lett. 37

      Pages: 1008-1009

    • NAID

      10024282862

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Thiochromans Based on Indirect Cation Pool Method2008

    • Author(s)
      Matsumoto, K.; Ueoka, K.: Fujie, S.; Yoshida, J.
    • Journal Title

      Heterocycles 76

      Pages: 1103-1119

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Practical Electrochemical Iodination of Aromatic Compounds2008

    • Author(s)
      Kataoka, K.; Hagiwara, Y.; Midorikawa, K.; Suga, S.; Yoshida, J.
    • Journal Title

      Org.Process Res.Dev. 12

      Pages: 1130-1136

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Initiated Cation Chain Reaction. Intramolecular Carbon-Carbon Bond Formation between Thioacetal and Olefin.2008

    • Author(s)
      Matsumoto, K.; Fujie, S.; Ueoka, K.; Suga, S.; Yoshida, J.
    • Journal Title

      Angew. Chem., Int. Ed. 47

      Pages: 2506-2506

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reaction of N-Acyliminium Ion Pool with Benzylsilane. Implication of a Radical/Cation/Radical Cation Chain Mechanism Involving Oxidative C-Si Bond Cleavage Maruyama2007

    • Author(s)
      T. ; Mizuno, Y. ; Shimizu, I. ; Suga, S. ; Yoshida
    • Journal Title

      J.J. Am. Chem. Soc. 129

      Pages: 1902-1903

    • Related Report
      2008 Final Research Report
  • [Journal Article] Reaction of N-Acyliminium Ion Pool with Benzylsilane. Implication of a Radical/Cation/Radical Cation Chain Mechanism Involving Oxidative C-Si Bond Cleavage2007

    • Author(s)
      Maruyama, T.; Mizuno, Y.; Shimizu, I.; Suga, S.; Yoshida, J.
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 1902-1903

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electrochemical Generation of Glycosyl Triflate Pools.2007

    • Author(s)
      Nokami, T.; Shibuya, A.; Tsuyama, H.; Suga, S.; Bowers, A. A.; Crich, D.; Yoshida, J.
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 10922-10928

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Indirect Cation Pool Method. Rapid Generation of Alkoxycarbenium Ion Pools from Thioacetals2006

    • Author(s)
      Suga, S. ; Matsumoto, K. ; Ueoka, K. ; Yoshida
    • Journal Title

      J.J. Am. Chem. Soc. 128

      Pages: 7710-7711

    • Related Report
      2008 Final Research Report
  • [Journal Article] Distannane Mediated Reaction of N-Acyliminium Ion Pools with Alkyl Halides. A Chain Mechanism Involving Radical2006

    • Author(s)
      Maruyama, T., Suga, S., Yoshida, J.
    • Journal Title

      Tetrahedron 62

      Pages: 6519-6525

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Indirect Cation Pool Method. Rapid Generation of Alkoxycarbenium Ion Pools from Thioacetals.2006

    • Author(s)
      Suga, S., Matsumoto, K., Ueoka, K., Yoshida
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 7710-7711

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Electroauxiliary-Assisted Sequential Introduction of Organic Groups on the ・-Carbons of Nitrogen.2006

    • Author(s)
      Suga, S., Watanabe, M., Song, C.-H., Yoshida, J.
    • Journal Title

      Electrochemistry 74

      Pages: 672-679

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Selective Monoiodination of Aromatic Compounds with Electrochemically Generated I+ Using Micromixing.2006

    • Author(s)
      Midorikawa, K., Suga, S., Yoshida, J.
    • Journal Title

      Chem. Commun.

      Pages: 3794-3796

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Oxidative Generation of Diarylcarbenium Ion Pools.2006

    • Author(s)
      Okajima, M., Soga, K., Nokami, T., Suga, S., Yoshida, J.
    • Journal Title

      Org. Lett. 6

      Pages: 5005-5007

    • Related Report
      2006 Annual Research Report
  • [Presentation] Electroorganic Synthesis Using Micro Reaction Systems2009

    • Author(s)
      Seiji Suga
    • Organizer
      International Symposium on Green and Sustainable Chemistry in Tottori
    • Year and Date
      2009-11-14
    • Related Report
      2008 Final Research Report
  • [Presentation] Cation Chain Reactions Initiated by Electrogenerated ArS+2009

    • Author(s)
      Kouichi Matsumoto, Shunsuke Fujie, Koji Ueoka, Seiji Suga, Jun-ichi Y
    • Organizer
      he 11th International Kyoto Conference on New Aspects of Organic Chemistry
    • Year and Date
      2009-11-12
    • Related Report
      2008 Final Research Report
  • [Presentation] マイクロフロー型電解セルを用いた有機活性種の発生と合成化学への展開2009

    • Author(s)
      菅誠治
    • Organizer
      第62回コロイドおよび界面化学討論会
    • Place of Presentation
      岡山理科大学
    • Year and Date
      2009-09-19
    • Related Report
      2008 Final Research Report
  • [Presentation] 高活性有機カチオンの化学とマイクロ反応プロセス2009

    • Author(s)
      菅誠治
    • Organizer
      有機合成化学協会中国四国支部第63回パネル討論会
    • Year and Date
      2009-05-16
    • Related Report
      2008 Final Research Report
  • [Presentation] 電解酸化により生じる有機イオウカチオン種を開始剤とするカチオン連鎖反応2009

    • Author(s)
      松本浩一、藤江駿介、菅誠治、吉田潤一
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学
    • Related Report
      2008 Final Research Report
  • [Presentation] カチオンプールと分子内に求核性官能基を有するオレフィンとの反応2009

    • Author(s)
      菅誠治、芦刈洋祐、上岡耕司、吉田潤一
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学
    • Related Report
      2008 Final Research Report
  • [Presentation] Stereoselective Cyclopropanation Reactions of N-Acyliminium Ion Pools with Alkenes2008

    • Author(s)
      Seiji Suga, Tomokazu Maruyama, Jun-ichi Yoshida
    • Organizer
      213th ECS Meeting
    • Place of Presentation
      Phoenix, USA Phoenix Convention Center
    • Year and Date
      2008-05-19
    • Related Report
      2008 Annual Research Report
  • [Presentation] 低温電解酸化により発生・蓄積させたアリールビス(アリールチオ)スルホニウムイオンとアルケンおよびアルキンの反応2008

    • Author(s)
      菅誠治、藤江駿介、松本浩一、吉田潤一
    • Organizer
      第32回有機電子移動化学討論会
    • Place of Presentation
      近畿大学
    • Related Report
      2008 Final Research Report
  • [Presentation] カチオンプール法を用いたテトラヒドロフラン環の立体選択的構築法2008

    • Author(s)
      菅誠治、芦刈洋祐、上岡耕司、吉田潤一
    • Organizer
      第32回有機電子移動化学討論会
    • Place of Presentation
      近畿大学
    • Related Report
      2008 Final Research Report
  • [Presentation] カチオンプール法に基づくテトラヒドロフラン環の構築法2008

    • Author(s)
      菅誠治、芦刈洋祐、木内洋平、竹内友也、上岡耕司、吉田潤一
    • Organizer
      電気化学会第75大会
    • Place of Presentation
      山梨大学
    • Related Report
      2008 Final Research Report
  • [Presentation] インダイレクトカチオンプール法を利用したチオクロマン類の合成2008

    • Author(s)
      松本浩一、菅誠治、吉田潤一
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Related Report
      2008 Final Research Report
  • [Presentation] インダイレクトカチオンプール法によるN-アシルイミニウムイオンプールの創製と利用2008

    • Author(s)
      菅誠治、上岡耕司、吉田潤一
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Related Report
      2008 Final Research Report
  • [Presentation] 低温電解酸化により発生・蓄積させたアリールビス(アリールチオ)スルホニウムイオンを用いたアルケンおよびアルキンのチオフルオロ化2008

    • Author(s)
      菅誠治、藤江駿介、吉田潤一
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Related Report
      2008 Final Research Report
  • [Presentation] カチオンプール法を用いたテトラヒドロフラン環の立体選択的構築法2008

    • Author(s)
      菅誠治、芦刈洋祐、上岡耕司、吉田潤一
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Related Report
      2008 Final Research Report
  • [Presentation] Synthesis of Diarylthio Compounds by the Reactions of Alkenes and Alkynes with Electrochemically Generated Arylbis(arylthio)sulfonium Ions2008

    • Author(s)
      Seiji Suga, Shunsuke Fujie, Kouichi Matsumoto, Jun-ichi Yoshida
    • Organizer
      213th ECS Meeting - Phoenix
    • Related Report
      2008 Final Research Report
  • [Presentation] Electro-Initiated Cationic Chain Reaction. Intramolecular C-C Bond Formation between Thioacetal and Olefin2008

    • Author(s)
      Kouichi Matsumoto, Shunsuke Fujie, Koji Ueoka, Seiji Suga, Jun-ichi Y
    • Organizer
      213th ECS Meeting - Phoenix
    • Related Report
      2008 Final Research Report
  • [Presentation] マイクロフローシステムを利用した高反応活性種の発生と反応制御2007

    • Organizer
      Combinatorial Chemistry研究会 第25回公開セミナー
    • Place of Presentation
      東工大
    • Year and Date
      2007-09-27
    • Related Report
      2008 Final Research Report
  • [Presentation] マイクロフローシステムを利用した高反応活性種の発生と反応制御2007

    • Author(s)
      菅 誠治
    • Organizer
      Combinatorial Chemistry研究会第25回公開セミナー
    • Place of Presentation
      東京工業大学
    • Year and Date
      2007-09-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] カチオンプール法に基づく含窒素ヘテロ環化合物の分子変換2007

    • Author(s)
      菅誠治、渡辺充、宋春紅、吉田潤一
    • Organizer
      第37回複素環化学討論会
    • Place of Presentation
      長野
    • Related Report
      2008 Final Research Report
  • [Presentation] 低温電解酸化により生じるアリールビス(アリールチオ)スルホニウムイオンを用いた分子変換2007

    • Author(s)
      松本浩一、上岡耕司、藤江駿介、菅誠治、吉田潤一
    • Organizer
      電気化学秋季大会
    • Place of Presentation
      東工大
    • Related Report
      2008 Final Research Report
  • [Presentation] カチオンプール法を用いたテトラヒドロフラン環形成反応2007

    • Author(s)
      菅誠治、芦刈洋祐、木内洋平、竹内友也、上岡耕司、吉田潤一
    • Organizer
      第31回有機電子移動化学討論会
    • Place of Presentation
      鳥取大学
    • Related Report
      2008 Final Research Report
  • [Presentation] 低温電解酸化により生じる有機イオウ活性種を用いたテトラヒドロピラン環形成反応2007

    • Author(s)
      松本浩一、上岡耕司、藤江駿介、菅誠治、吉田潤一
    • Organizer
      第31回有機電子移動化学討論会
    • Place of Presentation
      鳥取大学
    • Related Report
      2008 Final Research Report
  • [Presentation] 低温電解酸化により生じる有機イオウ活性種と炭素-炭素多重結合の反応2007

    • Author(s)
      菅誠治、藤江駿介、松本浩一、上岡耕司、吉田潤一
    • Organizer
      第31回有機電子移動化学討論会
    • Place of Presentation
      鳥取大学
    • Related Report
      2008 Final Research Report
  • [Presentation] 有機イオウ活性種を用いた炭素カチオンのマイクロフロー迅速発生法2007

    • Author(s)
      菅誠治、上岡耕司、松本浩一、吉田潤一
    • Organizer
      第31回有機電子移動化学討論会
    • Place of Presentation
      鳥取大学
    • Related Report
      2008 Final Research Report
  • [Presentation] 低温電解酸化により生じる有機イオウ活性種を用いたヘテロ環化合物の合成2007

    • Author(s)
      松本浩一、上岡耕司、藤江駿介、菅誠治、吉田潤一
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学
    • Related Report
      2008 Final Research Report
  • [Presentation] 低温電解酸化により生じる有機イオウ活性種とアルケンおよびアルキン類との反応2007

    • Author(s)
      菅誠治、藤江駿介、松本浩一、上岡耕司、吉田潤一
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学
    • Related Report
      2008 Final Research Report
  • [Presentation] 有機イオウ活性種を用いたアルコキシカルベニウムイオンのマイクロフロー迅速発生法2007

    • Author(s)
      菅誠治、上岡耕司、松本浩一、吉田潤一
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学
    • Related Report
      2008 Final Research Report
  • [Presentation] カチオンプール法を用いた新規ヘテロ環形成反応2007

    • Author(s)
      菅誠治、木内洋平、竹内友也、上岡耕司、吉田潤一
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学
    • Related Report
      2008 Final Research Report
  • [Presentation] Indirect Cation Pool Method. Rapid Generation of Alkoxycarbenium Ion Pools from Thioacetals2007

    • Author(s)
      Seiji Suga, Kouichi Matsumoto, Koji Ueoka, Jun-ichi Yoshida
    • Organizer
      ISOETC-2007, Keiko University
    • Related Report
      2008 Final Research Report
  • [Presentation] 電子移動反応により発生・蓄積した活性種を用いる合成化学2006

    • Author(s)
      菅誠治
    • Organizer
      第33回有機反応懇談会
    • Place of Presentation
      同志社大学
    • Year and Date
      2006-08-03
    • Related Report
      2008 Final Research Report
  • [Presentation] ジアリールジスルフィドの低温電解酸化により生じる活性種の構造と反応挙動2006

    • Author(s)
      松本浩一、菅誠治、上岡耕司、吉田潤一
    • Organizer
      第30回有機電子移動化学討論会
    • Place of Presentation
      東工大
    • Related Report
      2008 Final Research Report
  • [Presentation] ジアリールジスルフィドの低温電解酸化により生じる活性種を用いたカチオンプールの迅速発生法2006

    • Author(s)
      菅誠治、松本浩一、上岡耕司、吉田潤一
    • Organizer
      第30回有機電子移動化学討論会
    • Place of Presentation
      東工大
    • Related Report
      2008 Final Research Report
  • [Presentation] Indirect Cation Pool Method. Rapid Generation of Alkoxycarbenium Ion Pools from Thioacetals2006

    • Author(s)
      Koji Ueoka, Kouichi Matsumoto, Seiji Suga, Jun-ichi Yoshida
    • Organizer
      IKCOC10
    • Place of Presentation
      Kyoto
    • Related Report
      2008 Final Research Report
  • [Presentation] Arylbis(arylthio)sulfonium Ions Generated by Anodic Oxidation at Low Temperature2006

    • Author(s)
      Kouichi Matsumoto, Shunsuke Fujie, Koji Ueoka, Seiji Suga, Jun-ichi Y
    • Organizer
      IKCOC10
    • Place of Presentation
      Kyoto
    • Related Report
      2008 Final Research Report
  • [Presentation] Intramolecular Participation in Alkoxycarbenium Ion Pools2006

    • Author(s)
      Seiji Suga, Shinkiti Suzuki, Jun-ichi Yoshida
    • Organizer
      ISOR2006
    • Place of Presentation
      Kobe
    • Related Report
      2008 Final Research Report
  • [Book] マイクロリアクター利用に向いた有機合成反応(マイクロリアクターによる合成技術と工業生産)2009

    • Author(s)
      菅誠治
    • Publisher
      サエンス&テクノロジー社
    • Related Report
      2008 Final Research Report

URL: 

Published: 2006-04-01   Modified: 2016-04-21  

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