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Activation of Dipoles by Chiral 11 Group Metal Complexes and Diverse Oriented Synthesis

Research Project

Project/Area Number 25410053
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionChuo University

Principal Investigator

FUKUZAWA SHINICHI  中央大学, 理工学部, 教授 (50173331)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsアゾメチンイリド / 環化付加反応 / 共役付加反応 / キラル配位子 / キラル銀錯体触媒 / アミノ酸 / 多様性合成 / ドラッグディスカバリー / ピロリン / 共役付加 / ニトロアルケン / 不斉合成 / ピロリジン / スピロラクタム / 環化付加 / 双極子 / フェロセン / 1,3-双極子 / グリシンイミノエステル / キラルフェロセン / 酢酸銀 / 不斉触媒
Outline of Final Research Achievements

Optically active pyrrolidine derivatives are biologically active compounds and pharmaceutically important. Asymmetric 1,3-dipolar cycloaddition and conjugate addition of glycine iminoesters (azomethine ylide precursors) with active alkenes are effective for divers oriented synthesis of amino acid derivatives. Silver acetate/ThioClickFerrophos complex activates effectively azomethine ylide and catalyzes asymmetric 1,3-dipolar cycloaddition and conjugate addition reaction with active alkenes to afford optically active products with high stereoselection. The methodology can lead to diverse oriented synthesis of optically active amino acids and drug discovery.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (37 results)

All 2016 2015 2014 2013 Other

All Journal Article (9 results) (of which Acknowledgement Compliant: 6 results,  Peer Reviewed: 8 results) Presentation (27 results) (of which Int'l Joint Research: 2 results,  Invited: 2 results) Remarks (1 results)

  • [Journal Article] Bifunctional AgOAc/ThioClickFerrophos catalyzed asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides to nitroalkenes2016

    • Author(s)
      Kimura Midori, Matsuda Yukiko, Koizumi Akihiro, Tokoro Yuchiro, Fukuzawa Shin-ichi
    • Journal Title

      Tetrahedron

      Volume: 72

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Silver-catalyzed asymmetric Michael addition of azomethine ylide to arylidene diphosphonates using ThioClickFerrophos ligand2015

    • Author(s)
      Kimura Midori, Tada Atsuo, Tokoro Yuichiro, Fukuzawa Shin-ichi
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 17 Pages: 2251-2253

    • DOI

      10.1016/j.tetlet.2015.03.024

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
    • Acknowledgement Compliant
  • [Journal Article] Copper and silver catalyzed diastereo- and enantioselective conjugate addition reaction of 1-pyrroline esters to nitroalkenes2015

    • Author(s)
      Koizumi Akihiro, Kimura Midori, Arai Yuri, Tokoro Yuchiro, Fukuzawa Shin-ichi
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 80 Issue: 21 Pages: 10883-10981

    • DOI

      10.1021/acs.joc.5b02024

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of adamantyl substituted 1,2,3-triazol-5-ylidene ligands and their PEPPSI-type palladium complexes2015

    • Author(s)
      Mitsui Takashi. Sugihara Masato. Tokoro Yuichiro, Fukuzawa Shinichi
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 10 Pages: 1509-1514

    • DOI

      10.1016/j.tet.2015.01.040

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 7-azabicyclo[2.2.1]heptane-1-carboxylate via silver/ThioClickFerrophos-catalyzed asymmetric 1,3-dipolar cycloaddition of dihydropyrrole ester with N-substituted maleimide2014

    • Author(s)
      Tada Atsuo, Watanabe Sayo, Kimura Midori, Tokoro Yuichiro, Fukuzawa Shin-ichi
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 45 Pages: 6244-6226

    • DOI

      10.1016/j.tetlet.2014.09.070

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium/ClickFerrophos-Catalyzed Asymmetric Domino Allylstannylation-Heck Reaction of o-Formylaryl Triflate2014

    • Author(s)
      Tada Atsuo, Tokoro Yuichiro, Fukuzawa Shin-ichi
    • Journal Title

      Journal of Organic Chemistry

      Volume: 79 Issue: 17 Pages: 7905-7909

    • DOI

      10.1021/jo5010247

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Bifunctional AgOAc/ThioClickFerrophos complex-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with aryl- and alkylidene malonates2014

    • Author(s)
      Sayo Watanabe, Atsuo Tada, Yuichiro Tokoro, Shin-ichi. Fukuzawa
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 7 Pages: 1306-1309

    • DOI

      10.1016/j.tetlet.2013.12.101

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Silver/ThioClickFerrophos Complex as an Effective Catalyst for Asymmetric Conjugate addition of Glycine Imino Ester to Unsaturated Malonates and alpha-Enones2013

    • Author(s)
      Takashi Konno, Sayo Watanabe, Tatsuki Takahashi, Yuichiro Tokoro, Shin-ichi Fukuzawa
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 17 Pages: 4418-4421

    • DOI

      10.1021/ol4019584

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] N-heterocyclic carbene copper(I) complex-catalyzed direct C–H thiolation of benzothiazoles2013

    • Author(s)
      Hiroshi Inomata, Ayumi Toh, Takashi Mitsui, Shin-ichi Fukuzawa
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 35 Pages: 4729-4731

    • DOI

      10.1016/j.tetlet.2013.06.104

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] アルキニルフェロセニルエーテルとイソシアナートとのパラジ ウム触媒環化反応2016

    • Author(s)
      杉田健悟・所 雄一郎・福澤信 一・南 安規・檜山爲次郎
    • Organizer
      第 96 日本化学会春季年会
    • Place of Presentation
      同志社大学,京田辺
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Copper catalyzed Regioselective C-H Amination of Ferrocenes with Bidentate Directing Group2016

    • Author(s)
      Tokoro Yuichiro, Hoshino Shun, Fukuzawa, Shin-ichi
    • Organizer
      第 96 日本化学会春季年会
    • Place of Presentation
      同志社大学,京田辺
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] ラル銅・銀錯体触媒を用いたオキサゾリンおよびチアゾリンエステルとニトロアルケンへの不斉 共役付加反応2016

    • Author(s)
      小泉 昭紘・松田 結貴子・所 雄一郎・福澤 信一
    • Organizer
      第 96 日本化学会春季年会
    • Place of Presentation
      同志社大学,京田辺
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Enantio- and diastereoselective conjugate addition of 1-pyrroline 5-carboxylate esters to nitroalkenes catalyzed by silver and copper complexes with chiral ferrocenyl ligands.2015

    • Author(s)
      Kimura Midori, Fukuzawa Shin-ichi
    • Organizer
      PACHIFICHEM 2015
    • Place of Presentation
      ホノルル,ハワイ
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] キラル銀および銅錯体触媒を用いたピロリンエステルのニトロアルケンへの不斉 1,4-共役付加反応2015

    • Author(s)
      小泉 昭紘・木村 緑・新井 友梨・松田 結貴子・所 雄一郎・福澤 信一
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学,吹田
    • Year and Date
      2015-09-07
    • Related Report
      2015 Annual Research Report
  • [Presentation] パラジウム触媒によるアルキニルフェロセニルエーテルと内部アルキンとの環化付加反応2015

    • Author(s)
      杉田健吾,三井崇,所雄一郎,南安規,檜山為次郎,福澤信一
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学,吹田
    • Year and Date
      2015-09-07
    • Related Report
      2015 Annual Research Report
  • [Presentation] Enantio and Diastereoselective Conjugate addition of 1-Pyrroline 5-Carboxylate Esters to Nitoralkenes Catalyzed by Chiral Silver and Copper Complexes2015

    • Author(s)
      Koizumi Akio, Kimura Midori, Tokoro Yuichiro, Fukuzawa Shinichi
    • Organizer
      OMCOS18
    • Place of Presentation
      バルセロナ,スペイン
    • Year and Date
      2015-06-28
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] キラル銀及び銅錯体触媒を用いるピロリンエステルのニトロアルケンへの不斉マイケル付加反応2015

    • Author(s)
      小泉昭紘,木村 緑,所雄一郎,福澤信一
    • Organizer
      第69回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      横浜国立大学,横浜
    • Year and Date
      2015-05-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] ロジウム触媒によるC-H 結合切断を伴うフェニレンビスアセ トアミドと内部アルキンのクロスカップリング反応を利用した共役系 高分子の合成2015

    • Author(s)
      所雄一郎・佐藤滉・福澤信一
    • Organizer
      第 95 日本化学会春季年会
    • Place of Presentation
      日本大学,船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] キラル銀触媒を用いたピロリンエステルとニトロアルケンとの 1,4-共役付加反応2015

    • Author(s)
      小泉昭紘・木村緑・新井友梨・所 雄一郎・福澤信一
    • Organizer
      第 95 日本化学会春季年会
    • Place of Presentation
      日本大学,船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] アルキニルフェロセニルエーテルのパラジウム触媒によるC-H 結合活性化を経る内部アルキンとのアニュレーション反応2015

    • Author(s)
      三井崇・所雄一郎・檜山爲次郎・福澤信一
    • Organizer
      第 95 日本化学会春季年会
    • Place of Presentation
      日本大学,船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] キラルtzNHC 遷移金属錯体の合成と不斉水素移動反応への応 用2015

    • Author(s)
      登坂拓也・三井崇・所雄一郎・福澤信一
    • Organizer
      第 95 日本化学会春季年会
    • Place of Presentation
      日本大学,船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] ルテニウム触媒によるSi-H 結合とC-H 結合の切断を伴うナフ チルシランとアルキンの分子間環化反応2015

    • Author(s)
      杉田健悟・ 所雄一郎・福澤信一
    • Organizer
      第 95 日本化学会春季年会
    • Place of Presentation
      日本大学,船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] ジインとビフェニル誘導体の環化反応を利用した非平面構造を 有する多環芳香族炭化水素の合成とその光学特性2015

    • Author(s)
      大石杏奈・所雄一郎・福澤信一
    • Organizer
      第 95 日本化学会春季年会
    • Place of Presentation
      日本大学,船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis of 7-Azabicyclo[2.1.1]heptane-1-Carboxylate via Silver/ThioClickFerrophos-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Dihydropyrrole Ester with N-substituted Maleimide2014

    • Author(s)
      Atsuo Tada, Midori Kimura, Shin-ichi Fukuzawa
    • Organizer
      Vietnam Malaysia International Chemical Congress (VMICC) 2014
    • Place of Presentation
      ハノイ,ベトナム
    • Year and Date
      2014-11-07 – 2014-11-10
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] アダマンチル-1,2,3-トリアゾール-5-イリデ ン配位子の合成とカップリング反応への応用2014

    • Author(s)
      三井 崇・杉原 真人・所 雄一郎・福澤 信 一
    • Organizer
      第61回有機金属討論会
    • Place of Presentation
      九州大学,福岡
    • Year and Date
      2014-09-24 – 2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] 銀触媒を用いたジヒドロ-2H-ピロール-2-カルボ キシレートおよび 4-オキサゾールカルボキシレートと 活性アルケンとの不斉 1,3-双極子環化付加反応2014

    • Author(s)
      夛田 淳生・所 雄一郎・福澤 信一
    • Organizer
      第61回有機金属討論会
    • Place of Presentation
      九州大学,福岡
    • Year and Date
      2014-09-24 – 2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] Silver catalyzed asymmetric 1,3-dipolar cycloaddition of dihydro-2H-pyrrole-2-carboxylates or 4- oxazolecatboxylates with activated alkenes2014

    • Author(s)
      Atsuo Tada, Sayo Watanabe, Shinichi Fukuzawa
    • Organizer
      15th Tetrahedron Symposium
    • Place of Presentation
      London,イギリス
    • Year and Date
      2014-06-25 – 2014-06-27
    • Related Report
      2014 Research-status Report
  • [Presentation] Silver/ThioClickFerrophos catalyzed enantioselective 1,4-conjugate addition of glycine imino ester to aryl- and alkylidene phosphonates2014

    • Author(s)
      Midori Kimura, Shin-ichi Fukuzawa
    • Organizer
      15th Tetrahedron Symposium
    • Place of Presentation
      London,イギリス
    • Year and Date
      2014-06-25 – 2014-06-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 銀錯体触媒を用いたジヒドロピロールエステルの不斉1,3-双極子環化付加反応2014

    • Author(s)
      夛田淳生、渡部紗世、所雄一郎、福澤信一
    • Organizer
      第68回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      慶応大学,横浜
    • Year and Date
      2014-05-17
    • Related Report
      2014 Research-status Report
  • [Presentation] 銀/ThioClickFerrophos錯体触媒を用いたグリシンイミノエステルとアリーリデンホスホン酸とのエナンチオ選択的な1,4-共役付加反応2014

    • Author(s)
      木村緑、福澤信一
    • Organizer
      第68回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      慶応大学,横浜
    • Year and Date
      2014-05-17
    • Related Report
      2014 Research-status Report
  • [Presentation] Pd/ClickFerrophos錯体触媒を用いた不斉ドミノアリルスタニル化/Heck反応2013

    • Author(s)
      夛田淳生,緒方賢一, 福澤信一
    • Organizer
      第65回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟薬科大学
    • Related Report
      2013 Research-status Report
  • [Presentation] tzNHC-PEPPSI型パラジウム触媒の水中檜山カップリングへの応用2013

    • Author(s)
      三井崇,緒方賢一,福澤信一
    • Organizer
      第65回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟薬科大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Silver/ThioClickFerrophos Catalyzed Enantioselective Conjugate Addition and Cycloaddition of Glycine Imino Ester to Electron Deficient Alkenes2013

    • Author(s)
      Shin-ichi Fukuzawa, Takashi Konno, Kazumi Imae
    • Organizer
      14th Tetrahedron Symposium
    • Place of Presentation
      ウィーン,オーストリア
    • Related Report
      2013 Research-status Report
  • [Presentation] AgOAc/ThioClickFerrophos-Catalyzed Base Free Asymmetric Cycloaddition and Conjugate Addition with Imino Esters2013

    • Author(s)
      Sayo Watanabe, Takashi Konno, Kenichi Ogata, Shin-ichi Fukuzawa
    • Organizer
      17th Organometallic Chemistry Directed Toward Organic Synthesis
    • Place of Presentation
      フォートコリンズ,コロラド
    • Related Report
      2013 Research-status Report
  • [Presentation] キラル11族金属錯体触媒を用いた環状イミンと電子不足アルケンとの1,3-双極子環化付加反応2013

    • Author(s)
      渡辺紗世,夛田淳生,所雄一郎,福澤信一
    • Organizer
      第66回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京工業大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Palladium/ClickFerrophos Catalyzed Asymmetric Domino Allylstannlation-Heck Reaction of ortho-Formyltriflate2013

    • Author(s)
      Shin-ichi Fukuzawa, Atsuo Tada, Yuichiro Tokoro
    • Organizer
      International Symposium on Organic Reaction-11
    • Place of Presentation
      台北,台湾
    • Related Report
      2013 Research-status Report
    • Invited
  • [Remarks] FUKUZAWA Lab

    • URL

      http://www.chem.chuo-u.ac.jp/~fukuzawaweb/index.html

    • Related Report
      2015 Annual Research Report

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Published: 2014-07-25   Modified: 2019-07-29  

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