• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Efficient Synthesis of Enantiomerically Pure Amines by Highly Active Species

Research Project

Project/Area Number 25870458
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Chemical pharmacy
Research InstitutionOkayama University

Principal Investigator

MANDAI Hiroki  岡山大学, 自然科学研究科, 助教 (60534427)

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: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2013: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords光学活性アミン / 速度論的光学分割 / キラルブレンステッド酸 / 対アニオン制御型反応 / 速度論的光学分割反応 / アシル化反応 / キラルリン酸 / アシル化 / ピリジニウム塩 / 対アニオン / ラセミ体アミン
Outline of Final Research Achievements

We have interested in the development of the conceptually new approach for the kinetic resolution of amines. Especially reactions based on asymmetric counteranion-directed catalysis with chiral Brønsted acid are very attractive. We hypothesized that the chiral ion pairs derived from a chiral phosphate anion and achiral acylpyridinium salts should be good reactive species in enantioselective acylation of amines. We screened pyridine derivatives, solvents, and amount of reagents. As a result of this screening, the reaction system gave the product in 20% conversion with 82 : 18 er (s = 5.3).

Report

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

    (13 results)

All 2014 2013

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (9 results)

  • [Journal Article]2013

    • Author(s)
      Mitsudo、K.; Harada、J.; Tanaka、Y.; Mandai、H.; Nishioka、Tanaka、H.; Wakamiya、A.; Murata、Y.; Suga、S.
    • Journal Title

      J. Org. Chem

      Volume: 78 Issue: 6 Pages: 2763-8

    • DOI

      10.1021/jo302652r

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Kinetic Resolution of Secondary Alcohols by Chiral DMAP Derivatives Prepared by the Ugi Multicomponent Reaction2013

    • Author(s)
      Mandai, H.; Irie, S.; Akehi, M.; Yuri, K.; Yoden, M.; Mitsudo, K.; Suga, S.
    • Journal Title

      Heterocycles

      Volume: 87 Issue: 2 Pages: 329-340

    • DOI

      10.3987/com-12-12624

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Electro-reductive Halogen-Deuterium Exchange and Methylation of Aryl Halides in Acetonitrile2013

    • Author(s)
      Mitsudo, K.; Okada, T.; Shimohara, S.; Mandai, H.; Suga, S.
    • Journal Title

      Electrochemistry

      Volume: 81 Issue: 5 Pages: 362-364

    • DOI

      10.5796/electrochemistry.81.362

    • NAID

      10031152002

    • ISSN
      1344-3542, 2186-2451
    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Recyclable Palladium Catalyst in PEG/CH<sub>3</sub>CN Biphasic System for Electro-oxidative Wacker-type Reaction2013

    • Author(s)
      Mitsudo, K.; Fukunaga, S.; Fujita, T.; Mandai, H.; Suga, S.; Tanaka, H.
    • Journal Title

      Electrochemistry

      Volume: 81 Issue: 5 Pages: 347-349

    • DOI

      10.5796/electrochemistry.81.347

    • NAID

      10031151997

    • ISSN
      1344-3542, 2186-2451
    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Kinetic Resolution of Amines by the Asymmetric Counteranion-Directed Catalysis2014

    • Author(s)
      Kengo Goto, Hiroki Mandai, Seiji Suga
    • Organizer
      JSPS Bilateral Joint Research Seminar, Interdisciplinary Seminar for Innovative Organic Chemistry
    • Place of Presentation
      The University of Strasbourg
    • Year and Date
      2014-12-01 – 2014-12-03
    • Related Report
      2014 Annual Research Report
  • [Presentation] 求核触媒と共触媒の相乗効果を利用する分子内Morita-Baylis-Hillman反応の高速化2014

    • Author(s)
      下脇圭太,萬代大樹,菅誠治
    • 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] バイオジナス酸化鉄を用いた酸素分子によるBaeyer-Villiger反応2014

    • Author(s)
      萬代恭子,花田弥奈恵,光藤耕一,萬代大樹,橋本英樹,高田潤,菅誠治
    • 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] 軸不斉を有するキラルなDMAP 誘導体の創製および不斉Steglich 反応への適用2013

    • Author(s)
      萬代大樹,由利和信,明日卓,藤原卓真,是永敏伸,菅誠治
    • Organizer
      第43回 複素環化学討論会
    • Place of Presentation
      長良川国際会議場
    • Related Report
      2013 Research-status Report
  • [Presentation] 血管新生阻害剤(+)-terrein の効率的合成とヒト歯肉線維芽細胞におけるIL-6/sIL-6R 誘導性血管内皮増殖因子(VEGF) の阻害効果の検討2013

    • Author(s)
      萬代大樹,津村登紀,山本大介,大森一弘,高柴正吾,菅誠治
    • Organizer
      第30回 有機合成化学セミナー
    • Place of Presentation
      せとうち児島ホテル
    • Related Report
      2013 Research-status Report
  • [Presentation] バイオジナス酸化鉄固定化触媒を用いた反応開発2013

    • Author(s)
      萬代恭子,福田剛大,萬代大樹,宮崎祐樹,依馬正,橋本英樹,高田潤,菅誠治
    • Organizer
      第30回 有機合成化学セミナー
    • Place of Presentation
      せとうち児島ホテル
    • Related Report
      2013 Research-status Report
  • [Presentation] 新規キラルジアミン触媒による第二級アルコールの速度論的光学分割反応2013

    • Author(s)
      明日卓,萬代大樹,菅誠治
    • Organizer
      第30回 有機合成化学セミナー
    • Place of Presentation
      せとうち児島ホテル
    • Related Report
      2013 Research-status Report
  • [Presentation] 新しい不斉求核触媒の創製と触媒反応への展開2013

    • Author(s)
      萬代大樹
    • Organizer
      第2 回有機分子触媒若手セミナー
    • Place of Presentation
      ラフォーレ倶楽部伊東温泉湯の庭
    • Related Report
      2013 Research-status Report
  • [Presentation] Kinetic Resolution of Secondary Alcohols Using New Axially Chiral Diamine Catalysts2013

    • Author(s)
      Masaru Akehi, Hiroki Mandai, Seiji Suga
    • Organizer
      第1 回国際会議(兼) 第6 回有機触媒シンポジウム
    • Place of Presentation
      大津プリンスホテル
    • Related Report
      2013 Research-status Report

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi