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stereospecific cross-coupling reaction oriented toward efficient synthesis of non-naturally occurring amino acids

Research Project

Project/Area Number 25810061
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

TAKEDA Youhei  大阪大学, 工学(系)研究科(研究院), 助教 (60608785)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsアジリジン / クロスカップリング / アミノ酸 / パラジウム / ボリル化 / 位置選択的反応 / 立体特異的反応 / ボロン酸 / 不斉合成 / フェネチルアミン / N-ヘテロサイクリックカルベン
Outline of Final Research Achievements

A regioselective and enantiospecific cross-coupling reaction of N-tosyl-2-arylaziridines with arylboronic acids to give enantiopure 2-aryl-beta-phenethylamine derivatives in high yields has been realized under the effect of a catalytic amount of Pd complex bearing a NHC ligand. Under the similar reaction conditions, 2-carboxy ester-substituted aziridines underwent a regioselective cross-coupling to give non-naturally occurring beta-amino acid derivatives in moderate yields. Furthermore, a Pd-catalyzed regioselective ring-opening borylation of 2-arylaziridines has been found.

Report

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

    (13 results)

All 2014 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (12 results) (of which Invited: 1 results)

  • [Journal Article] Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki-Miyaura Arylation of 2-Arylaziridines: Synthesis of Enantioenriched 2-Arylphenethylamine Derivatives2014

    • Author(s)
      Youhei Takeda, Yuki Ikeda, Akinobu Kuroda, Shino Tanaka, and Satoshi Minakata
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 24 Pages: 8544-8547

    • DOI

      10.1021/ja5039616

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Presentation] Asymmetric Synthesis of 2-Arylphenetylamine Derivatives through a Pd-Catalyzed Enantiospecific Cross-coupling of 2-Arylaziridines with Arylboronic Acids2014

    • Author(s)
      Youhei Takeda, Akinobu Kuroda, Satoshi Minakata
    • Organizer
      15th Tetrahedron Symposium Asia Edition
    • Place of Presentation
      Singapore EXPO(シンガポール共和国南東地区)
    • Year and Date
      2014-10-28 – 2014-10-31
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd/Phosphine-Catalyzed Regioselective Borylation Reactions2014

    • Author(s)
      Akinobu Kuroda, Youhei Takeda, Satoshi Minakata
    • Organizer
      The 2nd International Conference on Organometallics and Catalysis (OM&Cat-2014)
    • Place of Presentation
      東大寺総合文化センター(奈良県奈良市)
    • Year and Date
      2014-10-26 – 2014-10-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd/ホスフィン触媒を用いたアジリジンの開環を伴う位置選択的ボリル化反応2014

    • Author(s)
      黒田明伸,武田洋平,南方聖司
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学 百年講堂(福岡県福岡市)
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd/ホスフィン触媒によるアジリジンの位置選択的開環を伴うホウ素化反応2014

    • Author(s)
      黒田明伸,武田洋平,南方聖司
    • Organizer
      第47回有機金属若手の会 夏の学校
    • Place of Presentation
      休暇村 大久野島(広島県竹原市)
    • Year and Date
      2014-09-01 – 2014-09-03
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki-Miyaura Cross-Coupling of 2-Arylaziridines with Arylboronic Acids to Construct a Tertiary Stereogenic Center2014

    • Author(s)
      Youhei Takeda
    • Organizer
      ICOMC 2014 Post-Symposium in Osaka
    • Place of Presentation
      大阪大学 銀杏会館(大阪府吹田市)
    • Year and Date
      2014-07-19
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Pd/Phosphine-Catalyzed Regioselective Borylative Ring-Opening Reaction of Aziridines2014

    • Author(s)
      Akinobu Kuroda, Youhei Takeda, Satoshi Minakata
    • Organizer
      ICOMC 2014 Post-Symposium in Osaka
    • Place of Presentation
      大阪大学 銀杏会館(大阪府吹田市)
    • Year and Date
      2014-07-19
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd/Phosphine-Catalyzed Regioselective Borylative Ring Opening Reaction of 2-Arylaziridines2014

    • Author(s)
      Akinobu Kuroda, Youhei Takeda, Satoshi Minakata
    • Organizer
      XXVI International Conference on Organometallic Chemistry (ICOMC 2014)
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] NHC/Pd-catalyzed Stereospecific and Regioselective Suzuki-Miyaura Arylative Cross-coupling Reaction of 2-Arylaziridines2014

    • Author(s)
      Youhei Takeda, Akinobu Kuroda, Satoshi Minakata
    • Organizer
      XXVI International Conference on Organometallic Chemistry (ICOMC 2014)
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] NHC/パラジウム触媒による2-アリールアジリジンのアリールボロン酸との立体特異的クロスカップリング反応

    • Author(s)
      武田洋平,黒田明伸,南方聖司
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Pd/NHC触媒を用いる2-アリールアジリジンの位置選択的かつ立体特異的鈴木宮浦カップリング反応

    • Author(s)
      武田洋平,黒田明伸,南方聖司
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2013 Research-status Report
  • [Presentation] NHC/Pd 触媒による 2-アリールアジリジ ンとアリールボロン酸の位置選択的かつ エナンチオ特異的クロスカップリング反応:2-アリールフェネチルアミン誘導体の不斉合成

    • Author(s)
      武田洋平,黒田明伸,南方聖司
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Pd触媒による2-アリールアジリジンの位置選択的開環を伴うボリル化反応

    • Author(s)
      武田洋平,田中詩乃,南方聖司
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report

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

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