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Dynamic Stereocontrolled Synthesis of Atropisomers via Highly Organized Hydrogen Bond Network

Research Project

Project/Area Number 25810025
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionTokyo University of Agriculture and Technology (2015)
Gakushuin University (2013-2014)

Principal Investigator

Mori Keiji  東京農工大学, 工学(系)研究科(研究院), 准教授 (10515076)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
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軸不斉ビアリール / 動的速度論的光学分割 / キラルリン酸触媒 / アトロプ異性体 / 還元的アミノ化 / 水素移動型還元反応 / 水素結合 / 動的立体制御
Outline of Final Research Achievements

Atropisomerism is very important chiral element, which can be seen in many useful organic molecules, such as biologically active compounds, chiral ligands, and organocatalysts. On the contrary to its usefulness, the method for asymmetric synthesis of atropisomers are scarce. Under such background, our group have been interested in the development of asymmetric synthesis of atropisomers by chiral phosphoric acid catalyzed dynamic kinetic resolution strategy. After extensive examination of the reaction conditions, we found that asymmetric reductive amination of biaryl lactols with o-hydroxyaniline were effectively catalyzed by chiral phosphoric acid with modified triarylsilyl group at 3,3’-positions to afford the desired biaryl-type benzyl amines in excellent enantioselectivities. Interestingly, the opposite enantiomer was obtained by simple changing position of the hydroxyl group in hydroxyaniline moiety from ortho- to meta-position.

Report

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

    (2 results)

All 2016

All Presentation (2 results) (of which Invited: 1 results)

  • [Presentation] キラルリン酸触媒を用いた動的速度論的光学分割を伴う軸不斉ビアリールの不斉合成2016

    • Author(s)
      森 啓二、板倉 翼、秋山 隆彦
    • Organizer
      第109回有機合成シンポジウム
    • Place of Presentation
      東京工業大学大岡山キャンパスディジタル多目的ホール(東京都目黒区)
    • Year and Date
      2016-06-08
    • Related Report
      2015 Annual Research Report
  • [Presentation] Asymmetric Synthesis of Chiral Biarlys based on the Highly Organized Hydrogen Bond Network Induced by Chiral Phosphoric Acid2016

    • Author(s)
      Keiji Mori
    • Organizer
      Workshop on Chirality in Chiba University (WCCU)
    • Place of Presentation
      千葉大学西千葉キャンパス自然科学総合研究棟1(千葉市稲毛区)
    • Year and Date
      2016-03-17
    • Related Report
      2015 Annual Research Report
    • Invited

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

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