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Research on Asymmetric Catalysis Based on Design and Synthesis of New Chiral Pincer-Type NHC Ligand

Research Project

Project/Area Number 26670007
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionWaseda University

Principal Investigator

Nakada Masahisa  早稲田大学, 理工学術院, 教授 (50198131)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords有機化学 / 不斉触媒反応 / NHC配位子
Outline of Final Research Achievements

We have established a synthetic method for the bisoxazoline-NHC-Ag(I) complex via concomitant formation of oxazolines and NHC using silver oxide, and the bisoxazoline-NHC-Ag(I) complex were converted to the corresponding pincer-type NHC-metal complexes. The NHC-Cr(III) complex showed no catalytic activity, but the dicationic NHC-Pt(II) complex catalyzed cycloisomerization of a 1,5-ene-yne albeit with low enantioselectivity. We have successfully synthesized a binaphthyl-fused imidazolylidene-AuCl complex and have found that the corresponding cationic complex catalyzes enantioselective cyclization of an ene-yne to afford quantitatively the product with 78% ee. Synthesis of the corresponding pincer-type binaphthyl-fused NHC ligands is now investigation.

Report

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

    (8 results)

All 2016 2015 2014 Other

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

  • [Journal Article] Research on the Design, Synthesis, and Catalytic Activity of Chiral N-Heterocyclic Carbene Ligand–Metal Complexes2016

    • Author(s)
      Usui, K.; Yoshida, T.; Nakada, M.
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 27 Issue: 2-3 Pages: 107-113

    • DOI

      10.1016/j.tetasy.2015.12.006

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of A New Chiral C2-Symmetric NHC-AuCl Complex2016

    • Author(s)
      Okitsu, N.; Yoshida, T.; Usui, K.; Nakada, M.
    • Journal Title

      Heterocycles

      Volume: 92 Issue: 4 Pages: 107-113

    • DOI

      10.3987/com-16-13408

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Characterizatoin of A New C2-Symmetrical Chiral Tridentate N-Heterocyclic Carbene Ligand Coordinated Cr(III) Complex2015

    • Author(s)
      Uetake, Y.;Niwa, T.; Nakada, M.
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 26 Issue: 2-3 Pages: 158-162

    • DOI

      10.1016/j.tetasy.2015.01.003

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 新規不斉ビナフチルNHC配位子の設計、合成とその金(I)錯体の触媒活性評価2016

    • Author(s)
      碓井 建佑 、吉田 拓也、中田 雅久
    • Organizer
      日本化学会第96春季年会(2016)
    • Place of Presentation
      京都
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] 新規不斉ビスービナフチルNHC配位子の設計、合成とその金(I)錯体の触媒活性評価2016

    • Author(s)
      沖津 直哉、吉田 拓也、碓井 建佑、中田 雅久
    • Organizer
      日本化学会第96春季年会(2016)
    • Place of Presentation
      京都
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis of C2-NHC Ligands and Their Application to Asymmetric Catalysis2014

    • Author(s)
      Kensuke USUI and Masahisa NAKADA
    • Organizer
      the XXVI International Conference on Organometallic Chemistry (ICOMC 2014)
    • Place of Presentation
      Sapporo, Hokkaido, Japan
    • Year and Date
      2014-07-15
    • Related Report
      2014 Research-status Report
  • [Remarks] 発表論文 PUBLICATIONS

    • URL

      http://www.chem.waseda.ac.jp/nakada/publications.html

    • Related Report
      2014 Research-status Report
  • [Remarks] PAPERS

    • URL

      http://www.chem.waseda.ac.jp/nakada/e-publications.html

    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2017-05-10  

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