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Development of cascade cyclization reaction via the direct activation of propargylalcohols

Research Project

Project/Area Number 26460009
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionTokushima Bunri University (2015-2016)
The University of Tokushima (2014)

Principal Investigator

YOSHIDA MASAHIRO  徳島文理大学, 薬学部, 教授 (10344681)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsプロパルギルアルコール / 活性化 / パラジウム / ルイス酸 / 求核剤 / 連続反応 / 連続的環化反応
Outline of Final Research Achievements

Propargylic compounds having an elimination group at the propargylic position are known as useful substrates in the palladium-catalyzed reactions. The reaction often employs activated propargylic alcohol derivatives such as propargylic esters, carbonates and halides, and no examples have been reported about the palladium-catalyzed reactions of underivatized propargylic alcohols with soft nucleophiles. The author developed palladium and boric acid-catalyzed cyclization of underivatized 1,3-diaryl propargylic alcohols with 1,3-cyclohexanediones. Boric acid plays a role for the efficient activation of the propargylic alcohols. Various substituted tetrahydrobenzofuranones were obtained in moderate to good yields. Reactions using 4-hydroxy-2-pyrones as the nucleophile also proceeded to afford the substituted dihydrofuropyranones.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (21 results)

All 2017 2016 2015 2014

All Journal Article (10 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 10 results,  Acknowledgement Compliant: 4 results,  Open Access: 1 results) Presentation (11 results) (of which Invited: 1 results)

  • [Journal Article] Syntheses of 2-Vinyl-2,3-dihydropyrroles and 3-Methylene-1,2,3,4-tetrahydropyridines by Palladium-Catalyzed Cyclization of N-Tosyl Imines with Allylic Diesters2017

    • Author(s)
      Masahiro Yoshida, Kouki Kinoshita, and Kosuke Namba
    • Journal Title

      Heterocycles

      Volume: 95 Issue: 1 Pages: 410-421

    • DOI

      10.3987/com-16-s(s)33

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Aerobic C-H Oxidation of Arenes Using a Recyclable, Heterogeneous Rhodium Catalyst2017

    • Author(s)
      Kenji Matsumoto, Shohei Tachikawa, Noriko Hashimoto, Rina Nakano, Masahiro Yoshida, and Mitsuru Shindo
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 8 Pages: 4305-4316

    • DOI

      10.1021/acs.joc.7b00300

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Synthesis of Cyclic Compounds by Palladium-Catalyzed Cyclization of Propargylic Esters with Nucleophiles2017

    • Author(s)
      吉田 昌裕
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 75 Issue: 1 Pages: 38-48

    • DOI

      10.5059/yukigoseikyokaishi.75.38

    • NAID

      130005296270

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct cyclization of 1,3-diaryl propargylic alcohols with dicarbonyl compounds by palladium-boric acid dual-catalyst system.2016

    • Author(s)
      Masahiro Yoshida, Shoko Ohno, Sayaka Eguchi, Tomotaka Mizuguchi, Kosuke Namba
    • Journal Title

      Tetrahedron

      Volume: 27 Issue: 36 Pages: 2591-2596

    • DOI

      10.1016/j.tet.2016.07.055

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of functionalized 2,3-dihydropyrroles by oxidative radical cyclization of N-sulfonyl β-enamino esters with alkenes.2016

    • Author(s)
      Masahiro Yoshida, Asuka Kobayashi, Atsushi Nakayama, Kosuke Namba
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 20 Pages: 2544-2551

    • DOI

      10.1016/j.tet.2016.03.055

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 2,3-Dihydro-4H-furo[3,2-c]chromen-4-one Derivatives by Oxidative Radical Cyclization of 4-Hydroxy-2H-chromen-2-one with Alkenes.2016

    • Author(s)
      Masahiro Yoshida, Asuka Kobayashi, Kosuke Namba
    • Journal Title

      Heterocycles

      Volume: 93 Issue: 2 Pages: 737-737

    • DOI

      10.3987/com-15-s(t)27

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Aerobic Oxidative Dehydrogenative Cross-Coupling: Nonsymmetrical Biaryl Amines.2016

    • Author(s)
      Kenji Matsumoto, Masahiro Yoshida, Mitsuru Shindo
    • Journal Title

      Angewandte Chemie, International Edition

      Volume: 55 Issue: 17 Pages: 5272-5276

    • DOI

      10.1002/anie.201600400

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Palau’amine2015

    • Author(s)
      K. Namba, K. Takeuchi, Y. Kaihara, M. Oda, A. Nakayama, A. Nakayama, M. Yoshida, and K. Tanino
    • Journal Title

      Nature Communications

      Volume: 6 Issue: 1 Pages: 8731-8731

    • DOI

      10.1038/ncomms9731

    • NAID

      120006999407

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Synthesis of functionalized 2-vinyl-2,3-dihydropyrroles and 3-methylene-1,2,3,4-tetrahydropyridines by palladium-catalyzed cyclization of ß-enaminocarbonyl compounds with allylic bisacetates2014

    • Author(s)
      Masahiro Yoshida, Kouki Kinoshita and Kosuke Namba
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 12 Issue: 15 Pages: 2394-2403

    • DOI

      10.1039/c3ob42510j

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total synthesis of (-)-HM-3 and (-)-HM-4 utilizing a palladium-catalyzed addition of an arylboronic acid to an allenic alcohol-Eschenmoser-Claisen rearrangement2014

    • Author(s)
      Masahiro Yoshida, Tomoyo Kasai, Tomotaka Mizuguti and Kosuke Namba
    • Journal Title

      Synlett

      Volume: 25 Issue: 08 Pages: 1160-1162

    • DOI

      10.1055/s-0033-1341059

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] N-アリールメチルプロパルギルアジリジンの開環・環化反応を鍵反応としたラスビンIIの全合成研究2017

    • Author(s)
      須藤彰太、水口智貴、廣兼司、松本健司、難波康祐、吉田昌裕
    • Organizer
      日本薬学会137年会
    • Place of Presentation
      仙台
    • Related Report
      2016 Annual Research Report
  • [Presentation] パラジウム触媒を用いた2-メチレン-1,3-プロパンジオールとβ-ジカルボニル化合物の環化反応2017

    • Author(s)
      江口彩香、廣兼司、松本健司、吉田昌裕
    • Organizer
      日本薬学会137年会
    • Place of Presentation
      仙台
    • Related Report
      2016 Annual Research Report
  • [Presentation] パラジウム触媒を用いたアリルジエステルと4-ヒドロキシ-2-ピロンの環化反応によるジヒドロピラノピラン骨格の構築2017

    • Author(s)
      古田絵莉香、向井達哉、廣兼司、松本健司、吉田昌裕
    • Organizer
      日本薬学会137年会
    • Place of Presentation
      仙台
    • Related Report
      2016 Annual Research Report
  • [Presentation] 含窒素芳香族化合物の触媒的ビアリールカップリング反応の開発2017

    • Author(s)
      松本健司、興梠彰太、酒井健太郎、新藤充、吉田昌裕
    • Organizer
      日本薬学会137年会
    • Place of Presentation
      仙台
    • Related Report
      2016 Annual Research Report
  • [Presentation] アルキニルアジリジンの 1,5-水素移動を鍵とする置換ピロリンの立体選択的合成2016

    • Author(s)
      水口智貴、和田文恵、中山淳、難波康祐、吉田昌裕
    • Organizer
      日本薬学会136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] アリールプロパルギルエーテルの不斉 [2+2] 環化付加反応の開発2016

    • Author(s)
      森岡亨平、加藤光貴、水口智貴、中山淳、難波康祐、吉田昌裕
    • Organizer
      日本薬学会136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] パラジウム触媒を用いたプロパルギルアルコールとβ-ジカルボニル化合物の環化反応2016

    • Author(s)
      江口彩香、大野祥子、水口智貴、難波康祐、吉田昌裕
    • Organizer
      日本薬学会136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] パラジウム触媒を用いたアリルジエステルと4-ヒドロキシ-2-ピロンの連続的環化反応2016

    • Author(s)
      向井達哉、古田絵莉香、廣兼司、松本健司、吉田昌裕
    • Organizer
      第55回日本薬学会中四国支部学術大会
    • Place of Presentation
      岡山
    • Related Report
      2016 Annual Research Report
  • [Presentation] アルキニルアジリジンの 1,5-水素移動を鍵とする置換ピリジン及びピペリジンの選択的合成2015

    • Author(s)
      水口智貴、中山淳、難波康祐、吉田昌裕
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      早稲田大学国際会議場(東京都新宿区)
    • Year and Date
      2015-11-19
    • Related Report
      2015 Research-status Report
  • [Presentation] パラジウム触媒を用いたプロパルギルアルコールと環状ジケトンの連続的環化反応2014

    • Author(s)
      大野祥子、吉田昌裕、難波康祐
    • Organizer
      第53回日本薬学会・日本薬剤師会・日本病院薬剤師会 中国四国支部学術大会
    • Place of Presentation
      広島国際会議場(広島県広島市)
    • Year and Date
      2014-11-08 – 2014-11-09
    • Related Report
      2014 Research-status Report
  • [Presentation] Palladium-Catalyzed Cyclization of Propargylic Esters with Nucleophiles2014

    • Author(s)
      Masahiro Yoshida
    • Organizer
      3rd International Conference on Organic Chemistry
    • Place of Presentation
      トビリシ(グルジア)
    • Year and Date
      2014-09-25 – 2014-09-28
    • Related Report
      2014 Research-status Report
    • Invited

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Published: 2014-04-04   Modified: 2018-03-22  

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