• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of novel domino reaction utilizing feature of highly reactive imtermediate 'borylenamine'

Research Project

Project/Area Number 22790028
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKobe Pharmaceutical University

Principal Investigator

UEDA Masafumi  神戸薬科大学, 薬学部, 講師 (00340935)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2010: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords合成化学 / ラジカル反応 / 共役イミン / ドミノ反応 / [3,3]-シグマトロピー転位 / benzofuro[2,3-b]pyrrole / ラクタム / 付加反応 / トリエチルボラン / 有機銅試薬 / 計算化学
Research Abstract

Reagent dependent regioselective additions to dual activated alkyne have been developed. The reaction with alkyl radical afforded β-addition product, while the reaction with organocuprate gave α-adduct with both high regio-and stereoselectivities. These reactions were applied to domino and one-pot reaction, providing tetrasubstituted and functionalized alkenes. Computational studies have been demonstrated to rationalize the selectivity.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (22 results)

All 2011 2010

All Journal Article (14 results) (of which Peer Reviewed: 5 results) Presentation (8 results)

  • [Journal Article] Copper(II) Chloride-Mediated Cyclization Reaction of N-Alkoxy-ortho-alkynylbenzamides2011

    • Author(s)
      Jithunsa, M.; Ueda, M.; Miyata, O.
    • Journal Title

      Org. Lett.

      Volume: 13(3) Pages: 518-521

    • Related Report
      2011 Final Research Report
  • [Journal Article] Benzyl Radical Addition Reaction through the Homolytic Cleavage of a Benzylic C-H Bond2011

    • Author(s)
      Ueda, M.; Kondoh, E.; Ito, Y.; Shono, H.; Kakiuchi, M.; Ichii, Y.; Kimura, T.; Miyoshi, T.; Naito, T.; Miyata, O.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 9(7) Pages: 2062-2064

    • Related Report
      2011 Final Research Report
  • [Journal Article] Silver-Catalyzed Synthesis of Disubstituted Isoxazoles by Cyclization of Alkynyl Oxime Ethers2011

    • Author(s)
      Ueda, M.; Ikeda, Y.; Sato, A.; Ito, Y.; Kakiuchi, M.; Shono, H.; Miyoshi, T.; Naito, T.; Miyata, O.
    • Journal Title

      Tetrahedron

      Volume: 67(25) Pages: 4612-4615

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Journal Article] Palladium-catalyzed Cross Coupling Reaction of N-Alkoxyimidoyl Bromides and Its Application to One-pot Synthesis of N-Arylamines2011

    • Author(s)
      Ueda, M.; Sugita, S.; Aoi, N.; Sato, A.; Ikeda, Y.; Miyoshi, T.; Naito, T.; Miyata, O.
    • Journal Title

      Chem. Pharm. Bull.

      Volume: 59(9) Pages: 1206-1208

    • NAID

      130001852331

    • Related Report
      2011 Final Research Report
  • [Journal Article] Regiodivergent Addition of Carbon Unit to Dual-Activated Alkynes for Stereoselective Construction of Tetrasubstituted Alkenes2011

    • Author(s)
      Ueda, M.; Matsubara, H.; Yoshida, K.; Sato, A.; Naito, T.; Miyata, O.
    • Journal Title

      Chem. Eur. J.

      Volume: 17(6) Pages: 1789-1792

    • Related Report
      2011 Final Research Report
  • [Journal Article] Copper(II)Chloride-Mediated Cyclization Reaction of N-Alkoxy-ortho-alkynylbenzamides2011

    • Author(s)
      Manita Jithunsa
    • Journal Title

      Org.Lett.

      Volume: 13(3) Pages: 518-521

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Benzyl Radical Addition Reaction through the Homolytic Cleavage of a Benzylic C-H Bond2011

    • Author(s)
      上田昌史
    • Journal Title

      Org.Biomol.Chem.

      Volume: 9(7) Issue: 7 Pages: 2062-2064

    • DOI

      10.1039/c0ob01148g

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Regiodivergent Addition of Carbon Unit to Dual-Activated Alkynes for Stereoselective Construction of Tetrasubstituted Alkenes.2011

    • Author(s)
      上田昌史
    • Journal Title

      Chem.Eur.J.

      Volume: 17(6) Pages: 1789-1792

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Synthesis of Trisubstituted Isoxazoles through Gold-Catalyzed Domino Reaction of Alkynyl Oxime Ethers2010

    • Author(s)
      Ueda, M.; Sato, A.; Ikeda, Y.; Naito, T.; Miyata, O.
    • Journal Title

      Org. Lett.

      Volume: 12(11) Pages: 2594-2597

    • Related Report
      2011 Final Research Report
  • [Journal Article] Indium(I)-Mediated Radical Carbon-Carbon Bond-Forming Reaction in Aqueous Media2010

    • Author(s)
      Ueda, M.; Miyabe, H.; Torii, M.; Kimura, T.; Miyata, O.; Naito, T.
    • Journal Title

      Synlett

      Volume: 9 Pages: 1341-1344

    • Related Report
      2011 Final Research Report
  • [Journal Article] Synthesis of Fluorinated Imines by Addition of Fluoroalkyl Radicals to Conjugated Imines2010

    • Author(s)
      Ueda, M.; Iwasada, E.; Miyabe, H.; Miyata, O.; Naito, T.
    • Journal Title

      Synthesis

      Volume: 12 Pages: 1999-2004

    • Related Report
      2011 Final Research Report
  • [Journal Article] Efficient Entry into 2-Substituted Tetrahydroquinoline Systems through Alkylative Ring Expansion : Stereoselective Formal Synthesis of(±)-Martinellic Acid2010

    • Author(s)
      Ueda, M.; Kawai, H ; Hayashi, M.; Naito, T.; Miyata, O.
    • Journal Title

      J. Org. Chem.

      Volume: 75(3) Pages: 914-921

    • Related Report
      2011 Final Research Report
  • [Journal Article] Synthesis of Fluorinated Imines by Addition of Fluoroalkyl Radicals to Conjugated Imines.2010

    • Author(s)
      上田昌史
    • Journal Title

      Synthesis

      Volume: (12) Pages: 1999-2004

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Synthesis of Trisubstituted Isoxazoles through Gold-Catalyzed Domino Reaction of Alkynyl Oxime Ethers2010

    • Author(s)
      上田昌史
    • Journal Title

      Org.Lett.

      Volume: 12(11) Pages: 2594-2597

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] ラジカル付加反応と[3,3]-シグマトロピー転位が連動する新規ドミノ型反応の開発2011

    • Author(s)
      宮田興子
    • Organizer
      第61回日本薬学会近畿支部総会・大会
    • Place of Presentation
      神戸
    • Year and Date
      2011-11-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] アルキニルN-アルコキシイミン類およびアミド類の遷移金属による閉環反応の開発2011

    • Author(s)
      上田昌史, Manita Jithunsa, 佐藤あおい, 三好哲也, 宮田興子
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島
    • Year and Date
      2011-11-07
    • Related Report
      2011 Final Research Report
  • [Presentation] ラジカル付加反応と[3, 3]-シグマトロピー転位が連動する新規ドミノ型反応の開発2011

    • Author(s)
      上田昌史, 伊藤勇太, 一井裕妃, 垣内麻衣子, 庄野裕子, 三好哲也, 宮田興子
    • Organizer
      第61回日本薬学会近畿支部総会・大会
    • Place of Presentation
      神戸
    • Year and Date
      2011-10-22
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthesis of Benzofuro [2, 3-b] pyrroles through a Radical Addition/ [3, 3]-Sigmatropic Rearrangement/Cyclization/Lactamization Cascade2011

    • Author(s)
      Masafumi Ueda, Yuta Ito, and Okiko Miyata
    • Organizer
      5th Pacific Symposium on Radical Chemistry
    • Place of Presentation
      和歌山
    • Year and Date
      2011-09-25
    • Related Report
      2011 Final Research Report
  • [Presentation] ベンジル位のC-H結合開裂反応による炭素ラジカルの生成と電子不足オレフィンへの付加反応2010

    • Author(s)
      上田昌史, 近藤瑛子, 三好哲也, 内藤猛章, 宮田興子
    • Organizer
      第60回日本薬学会近畿支部総会・大会
    • Place of Presentation
      枚方
    • Year and Date
      2010-10-30
    • Related Report
      2011 Final Research Report
  • [Presentation] Transition Metal-mediated Cyclization of N-Alkoxy-o-alkynylbenzamides for Chlorinated Heterocycles2010

    • Author(s)
      Jithunsa M., Ueda M., Miyata O.
    • Organizer
      The 6th International Symposium on Integrated Synthesis
    • Place of Presentation
      神戸
    • Year and Date
      2010-10-24
    • Related Report
      2011 Final Research Report
  • [Presentation] アルキニルオキシムエーテル類の遷移金属触媒を用いた閉環反応の開発:多置換イソキサゾール合成2010

    • Author(s)
      上田昌史, 佐藤あおい, 三好哲也, 内藤猛章, 宮田興子
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2010-10-15
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] Synthesis of Highly Substituted Isoxazoles through Transition Metal-Catalyzed Cyclization of Alkynyl Oxime Ethers2010

    • Author(s)
      Ueda M., Sato A., Miyoshi T., Naito T., Miyata O.
    • Organizer
      The 18th International Conference on Organic Synthesis
    • Place of Presentation
      Bergen
    • Year and Date
      2010-08-03
    • Related Report
      2011 Final Research Report

URL: 

Published: 2010-08-23   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi