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Survey and Development of Highly Active Catalysts for Environmentally Benign Synthesis of Optically Active 1,2-Diols

Research Project

Project/Area Number 25620076
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

NISHIYAMA HISAO  名古屋大学, 工学(系)研究科(研究院), 教授 (40135421)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords有機合成 / 不斉合成 / 光学活性化合物 / 有機金属 / 触媒 / 合成化学 / 環境融和 / 不斉触媒 / 酸化反応
Outline of Final Research Achievements

In organic synthesis, environmentally benign process has been pursued with no use of toxic materials and non precious metals. In this research, optically active 1,2-diols, which can be used as a starting materials for pharmaceutical and functional materials, can be synthesized by use of osmium salts. We examined asymmetric catalytic reaction with terminal alkenes and N,N,N-ligands. Using some of iron complexes and nitrogen ligands has been tried to obtain a small amount of epoxides and diol. On the other hand, the reaction through diboration followed by oxidation giving diols using chiral rhodium catalysts. Bis(oxazolnyl)phenyl-rhodium complex promoted successfully formation of diols from alkenes. In addition, 3-amino-1,2-diols were synthesized with the same Rh catalysts by using amido-, imide-, and carbamate-alkenes as substrates. Moreover, 1,2-disubstituted alkenes was tried by diboration to give the corresponding diols in good yields.

Report

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

    (7 results)

All 2015 2013 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 1 results) Presentation (3 results) (of which Invited: 2 results) Remarks (2 results)

  • [Journal Article] Asymmetric synthesis of optically active 3-amino-1,2-diols from N-acyl-protected allylamines cia catalytic diboration with Rh[bis(oxazolinyl)phenyl] catalysts2015

    • Author(s)
      Kenji Toribatake, Suguru Miyata, Yuki Naganawa, Hisao Nishiyama
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 21 Pages: 3203-3208

    • DOI

      10.1016/j.tet.2015.04.011

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric diboration of terminal alkenes with rhodium catalyst and subsequent oxidation: Enantioselective synthesis of optically active 1,2-diols2013

    • Author(s)
      Toribatake, K.; Nishiyama, H.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 52 Issue: 42 Pages: 11011-11015

    • DOI

      10.1002/anie.201305181

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 光学活性ロジウム錯体の不斉合成触媒としての多機能性2015

    • Author(s)
      西山久雄
    • Organizer
      第46回中部化学関係学協会支部連合秋季大会~特別討論会21世紀を拓く有機化学
    • Place of Presentation
      三重大学
    • Year and Date
      2015-11-07
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] アルケン類の不斉ジボリル化を経由する光学活性1,2-ジオールの合成法2013

    • Author(s)
      鳥畠賢二、西山久雄
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      静岡大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Asymmetric Synthesis of 1,2-Diols from Alkenes with Rhodium Catalyst via Diboration2013

    • Author(s)
      Hisao Nishiayma
    • Organizer
      Catalysis & Fine Chemicals 2013
    • Place of Presentation
      Renmin University of China, Beijin
    • Related Report
      2013 Research-status Report
    • Invited
  • [Remarks] abstract

    • URL

      http://www.apchem.nagoya-u.ac.jp/06-II-1/nisilab/Abstract.html

    • Related Report
      2015 Annual Research Report
  • [Remarks] Abstracts

    • URL

      http://www.apchem.nagoya-u.ac.jp/06-II-1/nisilab/Abstract.html

    • Related Report
      2013 Research-status Report

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

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