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Development of the innovative organic synthesis based on the hydrogen autotransfer process

Research Project

Project/Area Number 23550122
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic 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) ZHOU Da-yang  大阪大学, 産業科学研究所, 助教 (00324848)
ASANO Kaori  大阪大学, 産業科学研究所, 助教 (00311762)
Co-Investigator(Renkei-kenkyūsha) SASAI Hiroaki  大阪大学, 産業科学研究所, 教授 (90205831)
Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2011: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsタンデム反応 / アルドール反応 / ジオール / アルデヒド / 不斉触媒 / イリジウム / 水素自動移動プロセス / カスケード反応 / 水素移動反応 / 非対称化反応 / タンデムカップリング / 触媒的不斉合成 / 不斉合成 / 酸化反応 / 環境調和 / メソジオール / タンデム / ワンポットプロセス / Tishchenko
Research Abstract

Asymmetric tandem coupling of meso-diols with aldehydes was achieved by using a chiral iridium catalyst. This tandem reaction consists of oxidative desymmetrization of the meso-diol, aldol condensation with an aldehyde, and reduction of the enone intermediate. A one-pot method using an excess of a hydrogen donor gave a-benzyl-b-hydroxyindan-1-ones in <94% ee and 88% yield. An asymetric Hydrogen auto-transfer process in the absence of an addnl. H donor gave the desired benzyl ketone in 92% ee. The reaction intermediate enone was detected by using in situ IR spectroscopy.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (16 results)

All 2013 2012 2011 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (12 results) (of which Invited: 2 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Enantioselective Multicatalytic Synthesis of α-Benzyl-β-hydroxyindan-1-ones2013

    • Author(s)
      Suzuki, T.; Ishizaka, Y.; Ghozati, K.; Zhou, D.-Y.; Asano, K.; Sasai, H
    • Journal Title

      Synthesis

      Volume: (in press) Issue: 15 Pages: 2134-2136

    • DOI

      10.1055/s-0033-1338479

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Organic Synthesis Involving Iridium-Catalyzed Oxidation2011

    • Author(s)
      Suzuki, T.
    • Journal Title

      Chem. Rev.

      Volume: 111 Issue: 3 Pages: 1825-1845

    • DOI

      10.1021/cr100378r

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Presentation] Ir Catalyzed Asymmetric Tandem Reaction of meso-Diols and Aldehydes2013

    • Author(s)
      Suzuki, T.
    • Organizer
      Nagoya Symposium 2013
    • Place of Presentation
      Nagoya University, Nagoya
    • Year and Date
      2013-05-23
    • Related Report
      2013 Final Research Report
  • [Presentation] Ir Catalyzed Asymmetric Tandem Reaction of meso-Diols and Aldehydes2013

    • Author(s)
      Suzuki, T.
    • Organizer
      The 8th International Symposium on Integrated Synthesis (ISIS-8)
    • Place of Presentation
      Todaiji Temple Cultural Center, Nara
    • Related Report
      2013 Final Research Report
  • [Presentation] Ir Catalyzed Asymmetric Tandem Reaction of meso-Diols and Aldehydes2013

    • Author(s)
      Suzuki, T.
    • Organizer
      The 23rd French-Japanese Symposium on medicinal and fine chemistry (FJS2013)
    • Place of Presentation
      ANAクラウンプラザホテル長崎グラバーヒル
    • Related Report
      2013 Final Research Report
  • [Presentation] Ir Catalyzed Asymmetric Tandem Reaction of meso-Diols and Aldehydes2013

    • Author(s)
      Takeyuki Suzuki,
    • Organizer
      Tetrahedron Symposium
    • Place of Presentation
      Viena, Austria
    • Related Report
      2013 Annual Research Report
  • [Presentation] Ir Catalyzed Asymmetric Tandem Reaction of meso-Diols and Aldehydes2012

    • Author(s)
      Suzuki, T.
    • Organizer
      ICCOS-2012
    • Place of Presentation
      Zelinsky Institute of Organic Chemistry,Moscow, Russia
    • Related Report
      2013 Final Research Report
  • [Presentation] iridium-catalyzed asymmetrictandem reaction of meso-diol and aldehydes2012

    • Author(s)
      鈴木健之、石坂友香、Kazem Ghozati, 周 大揚、朝野芳織、笹井宏明
    • Organizer
      ICCOS-2012
    • Place of Presentation
      Moscow, Russia
    • Related Report
      2012 Research-status Report
  • [Presentation] iridium-catalyzed asymmetrictandem reaction of meso-diol and aldehydes2012

    • Author(s)
      鈴木健之、石坂友香、Kazem Ghozati, 周 大揚、朝野芳織、笹井宏明
    • Organizer
      FOC-2012
    • Place of Presentation
      St Petersburg, Russia
    • Related Report
      2012 Research-status Report
  • [Presentation] Ir-catalyzed asymmetrictandem reaction of meso-diol and aldehydes2012

    • Author(s)
      鈴木健之、石坂友香、Kazem Ghozati, 周 大揚、朝野芳織、笹井宏明
    • Organizer
      IKCOC-12
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Presentation] Ir Catalyzed Asymmetric Tandem Reaction of meso-Diols and Aldehydes2012

    • Author(s)
      鈴木健之、石坂友香、 周 大揚、朝野芳織、笹井宏明
    • Organizer
      有機金属化学討論会
    • Place of Presentation
      大阪
    • Related Report
      2012 Research-status Report
  • [Presentation] Ir catalyzed oxidative desymmetrization of diols2011

    • Author(s)
      Suzuki, T.
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学(愛知県名古屋)
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] Ir catalyzed oxidative desymmetrization of diols2011

    • Author(s)
      Suzuki, T.
    • Organizer
      2nd Annual World Congress of Catalytic Asymmetric Synthesis (WCCAS-2011)
    • Place of Presentation
      Beijing, China
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] Ir触媒を用いるメソジオールとアルデヒドの連続型不斉カップリング反応の開発

    • Author(s)
      鈴木 健之・石坂 友香・周 大揚・朝野 芳織・笹井 宏明
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2011 Research-status Report
  • [Book] Desymmetrization of meso diols. In Comprehensive Chirality, Vol.5(Yamamoto, H.; Carreira, E. M., Eds.)2012

    • Author(s)
      Suzuki, T.
    • Total Pages
      5648
    • Publisher
      Elsevier
    • Related Report
      2013 Final Research Report
  • [Remarks]

    • URL

      http://www.sanken.osaka-u.ac.jp/labs/cac/

    • Related Report
      2013 Final Research Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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