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Asymmetric molecular transformation using chiral onium amides

Research Project

Project/Area Number 25670002
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionTohoku University

Principal Investigator

KONDO Yoshinori  東北大学, 薬学研究科(研究院), 教授 (90162122)

Co-Investigator(Renkei-kenkyūsha) TANAKA Yoshiyuki  東北大学, 大学院薬学研究科, 准教授 (70333797)
INAMOTO Kiyofumi  武庫川女子大学, 薬学部, 准教授 (30359533)
KUMADA Kanako  東北大学, 大学院薬学研究科, 助手 (30748504)
Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsオニウムアミド / キラル / 不斉 / 分子変換 / 脱プロトン化 / 有機触媒 / 複素芳香環 / シンコナアルカロイド / キラルアンモニウム塩 / 不斉分子変換 / 芳香環 / 芳香複素環 / アンモニウム / ホスホニウム / 不斉変換 / 選択性
Outline of Final Research Achievements

Onium amides have been used for catalytic functionalization of heteroaromatic compoumds, which amides were generated in situ using a combination of onium fluorides and aminosilanes. Chiral onium amides prepared from chiral ammonium fluorides with aminosilanes or chiral phosophonium fluorides with aminosilanes. Enantioselective transformation of heteroarenes was investigated using these chiral onium amides, .

Report

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

    (11 results)

All 2015 2014 2013 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Acknowledgement Compliant: 3 results) Presentation (5 results) (of which Invited: 2 results) Remarks (2 results)

  • [Journal Article] Deprotonative C-H solylation of functionalizaed arenes and heteroarenes using trimethyl -trialkylsilane with fluoride2015

    • Author(s)
      Sasaki, Midori; Kondo, Yoshinori
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 4 Pages: 848-851

    • DOI

      10.1021/ol503671b

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Use of tetramehylammonium fluoride (TMAF) and alkali metal alkoxides as an activator for catalytic deprotonative functionalization of heteroaromatic C(sp2)-H2014

    • Author(s)
      Inamoto, Kiyofumi; Okawa, Hitomi; Kikkawa, Shoko; Kondo, Yoshinori,
    • Journal Title

      Tetrahedron

      Volume: 70 Issue: 43 Pages: 7917-7922

    • DOI

      10.1016/j.tet.2014.08.054

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct condensation of functionalized sp3 carbons with formamides for enamine synthesis using an in situ generated HMDS amide catalyst2014

    • Author(s)
      Taneda, Hiroshi; Inamoto, Kiyofumi; Kondo, Yoshinori
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 49 Pages: 6523-6525

    • DOI

      10.1039/c4cc02228a

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Organocatalytic functionalization of heteroaromatic N-oxides with C-nucleophiles using in situ generated onium amide bases2013

    • Author(s)
      Kiyofumi Inamoto, Yuta Araki, Shoko Kikkawa, Misato Yonemoto, Yoshiyuki Tanaka, Yoshinori Kondo
    • Journal Title

      Organic &Biomolecular Chemistry

      Volume: 11 Issue: 27 Pages: 4438-4441

    • DOI

      10.1039/c3ob40782a

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] トリフルオロメチルシラン活性化を介した芳香族ケイ素化反応2014

    • Author(s)
      佐々木碧、根東義則
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2014-11-10 – 2014-11-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] フッ化オニウムを用いる芳香族ハロゲン化合物の脱ハロゲン化及び修飾反応2014

    • Author(s)
      中村亘佑、根東義則
    • Organizer
      第53回日本薬学会東北支部大会
    • Place of Presentation
      いわき
    • Year and Date
      2014-10-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] アンモニウム塩を用いた複素環化合物のラジカル的カップリング反応2014

    • Author(s)
      山田哲也、根東義則
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      札幌
    • Year and Date
      2014-09-11 – 2014-09-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] 芳香族ハロゲン化合物のメタルフリー脱ハロゲン化反応2014

    • Author(s)
      中村亘佑、佐々木碧、吉川晶子、根東義則
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学黒髪キャンパス
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 芳香族ケイ素化合物のカルボキシル化反応2013

    • Author(s)
      小林みさと、稲本浄文、根東義則
    • Organizer
      第52回日本薬学会東北支部大会
    • Place of Presentation
      東北大学川内キャンパス
    • Related Report
      2013 Research-status Report
    • Invited
  • [Remarks] 分子変換化学分野

    • URL

      http://www.pharm.tohoku.ac.jp/~henkan/lab/henkan_top.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 分子変換化学分野

    • URL

      http://www.tohoku.ac.jp/~henkan/lab/henkan_top.html

    • Related Report
      2013 Research-status Report

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

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