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Development and application of asymmetric redox cascade reaction using iridium catalyst

Research Project

Project/Area Number 17K05784
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

Suzuki Takeyuki  大阪大学, 産業科学研究所, 准教授 (10262924)

Co-Investigator(Kenkyū-buntansha) 朝野 芳織  大阪大学, 産業科学研究所, 助教 (00311762)
周 大揚  大阪大学, 産業科学研究所, 助教 (00324848)
Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsレドックスカスケード / イリジウム / Tishchenko反応 / 還元 / 酸化 / ラクトン / 不斉合成 / 不斉触媒 / 酸化反応 / 還元反応 / 質量分析 / Tishchenko反応 / メソジアルデヒド / エンテロラクトン / Tishchenko 反応 / セダルマイシン / 有機化学
Outline of Final Research Achievements

Asymmetric Tishchenko-type reaction was realized as a redox-neutral asymmetric cascade reaction using a chiral iridium catalyst. As an application of this reaction, we succeeded in the catalytic asymmetric synthesis of the cedarmycin from the optically active lactone product. In order to investigate the structure of catalytically active species in the asymmetric Tishchenko type reaction, cold spray ionization mass spectrometry was investigated and reaction intermediates was observed.

Academic Significance and Societal Importance of the Research Achievements

本技術は環境調和型反応として実用性にも優れ、キラルテクノロジーとしても魅力的である。医薬品など有用化合物には多数の不斉中心を含むものも多く、本研究が目指す不斉合成法は将来の創薬研究に対しても有効な手法となる。このように、不斉レドックスカスケード反応を開発できれば、合成化学的応用が広く、触媒的不斉合成法の新たな潮流となることが期待される。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (4 results)

All 2019 2018 2017

All Presentation (4 results) (of which Int'l Joint Research: 4 results)

  • [Presentation] Synthetic study of enterolactone using chiral iridium complex2019

    • Author(s)
      鈴木健之
    • Organizer
      Tetrahedron symposium
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Catalytic Asymmetric Synthesis of Cedarmycins Using Chiral Iridium Complex2018

    • Author(s)
      鈴木健之
    • Organizer
      Tetrahedron symposium
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Catalytic asymmetric synthesis of cedarmycins using chiral iridium complex2018

    • Author(s)
      鈴木健之
    • Organizer
      XXII International Conference on Organic Synthesis
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Catalytic Asymmetric Synthesis of Natural Products Using Ir Catalyzed Tishchenko-type Reaction2017

    • Author(s)
      Takeyuki Suzuki, Ismiyarto,Takahiro Doi, Naoki Kishi, Da-yang Zhou, Kaori Asano, Yasushi Obora, Hiroaki Sasai
    • Organizer
      Tetrahedron symposium
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research

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Published: 2017-04-28   Modified: 2021-02-19  

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