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Development of novel reactions using iron catalyst and silicon reagents

Research Project

Project/Area Number 24790016
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionGifu Pharmaceutical University

Principal Investigator

SAWAMA Yoshinari  岐阜薬科大学, 薬学部, 助教 (80552413)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords鉄触媒 / シリル系試薬 / 環開裂反応 / ナフタレン / 脱離基 / 創薬指向型研究 / シリコン試薬 / 新規有機反応開発
Research Abstract

Since iron is inexpensive and safe, the development of the novel organic reactions using iron catalyst is valuable. We newly established two type iron-catalyzed reactions. (1) The iron-catalyzed functionalizations of tetrahydrofurans and oxanorbornadiene derivatives accompanied with the ring-opening of carbon-oxygen bonds can provide the pharmaceutically useful skeltones. (2) Although the siloxy and methoxy groups possess the low abilities as leaving groups, we discovered that the siloxy and methoxy groups could be easily eliminated by the use of iron catalyst to give the various products. This methodology is valuable to enable the reduction of cost and synthetic steps.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (34 results)

All 2014 2013 2012

All Journal Article (10 results) (of which Peer Reviewed: 5 results) Presentation (24 results) (of which Invited: 2 results)

  • [Journal Article] Chemoselective and Direct Functionalizationof Methyl Benzyl Ethers andUnsymmetrical Dibenzyl Ethers by Using Iron Trichloride Chem2014

    • Author(s)
      Yoshinari Sawama, Ryota Goto, Saori Nagata, Yuko Shishido, Yasunari Monguchi, Hironao Sajiki
    • Journal Title

      Eur. J.

      Volume: 20 Pages: 2631-2636

    • Related Report
      2013 Final Research Report
  • [Journal Article] Iron-Catalyzed Friedel?Crafts Benzylation with Benzyl TMS Ethersat Room Temperature Chem2014

    • Author(s)
      Yoshinari Sawama, Yuko Shishido, Takahiro Kawajiri, Ryota Goto, Yasunari Monguchi, Hironao Sajiki
    • Journal Title

      Eur. J.

      Volume: 20 Pages: 510-516

    • Related Report
      2013 Final Research Report
  • [Journal Article] Chemoselective and Direct Functionalization of Methyl Benzyl Ethers and Unsymmetrical Dibenzyl Ethers by Using Iron2014

    • Author(s)
      Yoshinari Sawama,* Ryota Goto, Saori Nagata, Yuko Shishido, Yasunari Monguchi, and Hironao Sajiki
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 9 Pages: 2631-2636

    • DOI

      10.1002/chem.201303910

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Friedel–Crafts Benzylation with Benzyl TMS Ethers at Room Temperature2014

    • Author(s)
      Yoshinari Sawama,* Yuko Shishido, Takahiro Kawajiri, Ryota Goto, Yasunari Monguchi, and Hironao Sajiki*
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 2 Pages: 510-516

    • DOI

      10.1002/chem.201302862

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Ring-Opening Azidation and Allylation of O-Heterocycle2013

    • Author(s)
      Yoshinari Sawama, Kyoshiro Shibata, Yuka Sawama, Masato Takubo, Yasunari Monguchi, Norbert Krause, Hironao Sajiki
    • Journal Title

      Org. Lett.

      Volume: 15 Pages: 5282-5285

    • Related Report
      2013 Final Research Report
  • [Journal Article] Lewis Acid-Catalyzed Ring-Opening Functionalizations of 1,4-Epoxy-1,4-dihydronaphthalenes2013

    • Author(s)
      Yoshinari Sawama, Yuta Ogata, Koichi Kawamoto, Hiroyuki Satake, Kyoshiro Shibata, Yasunari Monguchi, Hironao Sajiki, Yasuyuki Kita
    • Journal Title

      Adv. Synth. Catal.

      Volume: 355 Pages: 517-528

    • Related Report
      2013 Annual Research Report 2013 Final Research Report 2012 Research-status Report
  • [Journal Article] Efficient Generation of ortho- Naphthoquinone Methides from 1,4-Epoxy-1,4-dihydronaphthalenes and Their Annulation with AllylSilanes Angew2013

    • Author(s)
      Yoshinari Sawama, Yuko Shishido, Takayoshi Yanase, Koichi Kawamoto, Ryota Goto,Yasunari Monguchi, Yasuyuki Kita, Hironao Sajiki
    • Journal Title

      Chem. Int. Ed.

      Volume: 52 Pages: 1515-1519

    • Related Report
      2013 Final Research Report
  • [Journal Article] Iron-Catalyzed Ring-Opening Azidation and Allylation of O‑Heterocycles2013

    • Author(s)
      Yoshinari Sawama,* Kyoshiro Shibata, Yuka Sawama, Masato Takubo, Yasunari Monguchi, Norbert Krause, and Hironao Sajiki*
    • Journal Title

      Org. Lett

      Volume: 15 Issue: 20 Pages: 5282-5285

    • DOI

      10.1021/ol402511r

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of efficient generation method of ortho-naphthoquinone methides derived from 1,4-epoxy-1,4-dihydronaphthalenes and its unique annulation using allylsilanes2013

    • Author(s)
      Y. Sawama, Y. Kita et al.
    • Journal Title

      Angewandte Chemie,International Edition

      Volume: 52 Issue: 5 Pages: 1515-1519

    • DOI

      10.1002/anie.201207315

    • Related Report
      2013 Annual Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Chemoselective Azidation of Benzylic Silyl Ethers2012

    • Author(s)
      Y. Sawama, S. Nagata, Y. Yabe, K. Morita, Y. Monguchi, H. Sajiki
    • Journal Title

      Chem. Eur. J.

      Volume: 18 Pages: 16608-16611

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Iron-Catalyzed Chemoselective Azidation of Silyl Ethers2013

    • Author(s)
      Saori Nagata, Yoshinari Sawama, Yuki Yabe, Kosuke Morita, Yasunari Monguchi, Hironao Sajiki
    • Organizer
      Nagoya Symposium
    • Place of Presentation
      名古屋大学
    • Year and Date
      2013-05-23
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] Efficient Generation of ortho-Naphthoquinone Methides from 1,4-Epoxy-1,4-dihydronaphthalenes and Their Annulation with Allyl Silanes2013

    • Author(s)
      Yuko Shishido, Yoshinari Sawama, Ryota Goto, Yasunari Monguchi, Hironao Sajiki
    • Organizer
      Nagoya Symposium
    • Place of Presentation
      名古屋大学
    • Year and Date
      2013-05-23
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] 水酸基保護体の直接的官能基変換法の開発2013

    • Author(s)
      澤間善成、宍戸裕子、後藤諒太、永田沙織、門口泰也、佐治木弘尚
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] Lewis Acid-Catalyzed Ring-Opening Functionalizations of 1,4-Epoxy-1,4-dihydronaphthalenes2013

    • Author(s)
      Yoshinari Sawama, Yuta Ogata, Yasunari Monguchi, Hironao Sajiki
    • Organizer
      24th International Society of Heterocyclic Chemistry Congress (24th ISHC-Congress)
    • Place of Presentation
      上海
    • Related Report
      2013 Final Research Report
  • [Presentation] Generation of ortho-Naphthoquinone Methides from 1,4-Epoxy-1,4-dihydronaphthalenes and Their Annulation with Allyl Silanes2013

    • Author(s)
      Yuko Shishido, Yoshinari Sawama, Ryota Goto, Yasunari Monguchi, Hironao Sajiki
    • Organizer
      24th International Society of Heterocyclic Chemistry Congress (24th ISHC-Congress)
    • Place of Presentation
      上海
    • Related Report
      2013 Final Research Report
  • [Presentation] ベンジルTMSエーテルを基質とした室温下でのFriedel-Craftsベンジル化反応2013

    • Author(s)
      宍戸裕子、澤間善成、川尻貴大、後藤諒太、門口泰也、佐治木弘尚
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      浜松
    • Related Report
      2013 Final Research Report
  • [Presentation] 鉄触媒によるメチルならびにベンジルエーテルの直接的官能基変換法の開発2013

    • Author(s)
      後藤諒太、澤間善成、永田沙織、門口泰也、佐治木弘尚
    • Organizer
      日本プロセス化学会2013サマーシンポジウム
    • Place of Presentation
      浜松
    • Related Report
      2013 Final Research Report
  • [Presentation] Lewis Acid-Catalyzed Ring-Opening Functionalizations of 1,4-Epoxy-1,4-dihydronaphthalenes2013

    • Author(s)
      澤間 善成
    • Organizer
      The 24th International Society of Heterocyclic Chemistry Congress
    • Place of Presentation
      上海
    • Related Report
      2013 Annual Research Report
  • [Presentation] Generation of ortho-Naphthoquinone Methides from 1,4-Epoxy-1,4-dihydronaphthalenes and Their Annulation with Allyl Silanes2013

    • Author(s)
      宍戸裕子
    • Organizer
      The 24th International Society of Heterocyclic Chemistry Congress
    • Place of Presentation
      上海
    • Related Report
      2013 Annual Research Report
  • [Presentation] ベンジルTMSエーテルを基質とした室温下でのFriedel-Craftsベンジル化反応2013

    • Author(s)
      宍戸裕子
    • Organizer
      第44回 中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      浜松
    • Related Report
      2013 Annual Research Report
  • [Presentation] 鉄触媒によるメチルならびにベンジルエーテルの直接的官能基変換法の開発2013

    • Author(s)
      後藤諒太
    • Organizer
      日本プロセス化学会2013サマーシンポジウム
    • Place of Presentation
      筑波
    • Related Report
      2013 Annual Research Report
  • [Presentation] 鉄ーシリコンが介在する効率的有用骨格構築法の開発2013

    • Author(s)
      ○澤間善成
    • Organizer
      第1回創薬基盤化学研究セミナー
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 1,4-エポキシ-1,4-ジヒドロナフタレン類への環開裂型官能基導入法の開発2013

    • Author(s)
      ○緒方祐太、澤間善成、川本康一、佐竹弘行、柴田恭司郎、門口泰也、佐治木弘尚、北 泰行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] オルトナフトキノンメチドの効率合成法とアリルシランによる環化付加反応2013

    • Author(s)
      ○宍戸裕子、澤間善成、栁瀬考由、川本康一、後藤諒太、門口泰也、北 泰行、佐治木弘尚
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] メチルエーテルを基質とした鉄触媒による直接的アジド変換反応の開発2013

    • Author(s)
      澤間善成、○後藤諒太、永田沙織、門口泰也、佐治木弘尚
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] ヘテロ環の環開裂を伴う官能基化:アジド基導入反応を中心に2012

    • Author(s)
      ○澤間善成、緒方祐太、柴田恭司郎、門口泰也、佐治木弘尚、Norbert Krause 、北 泰行
    • Organizer
      第10回次世代シンポジウム
    • Place of Presentation
      大阪
    • Related Report
      2012 Research-status Report
  • [Presentation] 天然物合成に学ぶ新規反応の開発:ヘテロ環の環開裂型官能基化2012

    • Author(s)
      ○澤間 善成
    • Organizer
      平成24年度 有機合成化学協会東海支部若手研究者のためのセミナー
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] オルトナフトキノンメチドの効率的合成に次ぐアリルシランによる環化付加反応2012

    • Author(s)
      澤間 善成, 宍戸 裕子, 栁瀬 考由, 門口 泰也, 佐治木 弘尚, 川本 康一, 北 泰行
    • Organizer
      第38回 反応と合成の進歩シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] Development of efficient preparation method of ortho-naphthoquinone methidesand its unique annulation using allylsilanes2012

    • Author(s)
      ○Yoshinari Sawama, Yuko Shishido, Takayoshi Yanase, Ryota Goto, Yasunari Monguchi, Hironao Sajiki, Koichi Kawamoto, Yasuyuki Kita
    • Organizer
      IKCOC-12
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Presentation] 1,4-エポキシ-1,4-ジヒドロナフタレン類の開環を伴うルイス酸触媒的官能基導入反応2012

    • Author(s)
      ○緒方祐太、澤間善成、川本康一、佐竹弘行、門口泰也、北 泰行、佐治木弘尚
    • Organizer
      第58回薬学会東海支部大会
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report
  • [Presentation] 鉄触媒によるシリルエーテルからアジドへの選択的官能基変換2012

    • Author(s)
      澤間 善成,○永田沙織,矢部雄貴,森田康介,門口泰也,佐治木弘尚
    • Organizer
      第38回 反応と合成の進歩シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] FeCl3/TMSN3-induced direct azidation of benzylic silyl ethers2012

    • Author(s)
      Yoshinari Sawama, ○Saori Nagata, Yuki Yabe, Kosuke Morita, Yasunari Monguchi, Hironao Sajiki
    • Organizer
      IKCOC-12
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Presentation] オルトナフトキノンメチドの新規合成法の開発とアリルシランを用いた環化付加反応への応用2012

    • Author(s)
      澤間 善成、○宍戸 裕子、柳瀬 孝由、川本康一、門口泰也、北泰行、佐治木弘尚
    • Organizer
      第58回薬学会東海支部大会
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report
  • [Presentation] テトラヒドロフラン類の開環を伴う触媒的官能基導入法の開発2012

    • Author(s)
      〇柴田恭司郎、澤間善成、門口泰也、佐治木弘尚
    • Organizer
      第58回薬学会東海支部大会
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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