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Development of novel chiral catalyst with C2 symmetric ladder-type skeleton and its application to asymmetric catalysis

Research Project

Project/Area Number 17K08226
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionMeiji Pharmaceutical University

Principal Investigator

Saito Nozomi  明治薬科大学, 薬学部, 教授 (80349258)

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: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords触媒的不斉合成 / 環化反応 / 多環式化合物 / 相間移動触媒 / 不斉反応素子 / C2対称性 / ルテニウム / アレン / アルキン / 環化二量化 / 不斉アルキル化 / キラル合成素子 / アンモニウム塩 / 光学活性体 / 環化二量化反応 / C2対称 / ラダー状分子 / 有機分子触媒
Outline of Final Research Achievements

Asymmetric catalysis is widely recognized as a powerful and efficient methodology for the synthesis of organic molecules as an optically active form. We previously reported ruthenium-catalyzed cyclodimerizatino of 1,7-allenynes leading to a pentacyclotetradecane derivatives having a C2-symmteric skeleton. In order to develop a new class of chiral catalyst for asymmetric synthesis, we conducted synthetic study on the ladder-type skeleton-based molecules having a C2 symmetry. As a result, we succeeded in developing a new bis-ammonium salt as a phase transfer catalyst, which had pentacyclotetradecane skeleton.

Academic Significance and Societal Importance of the Research Achievements

我々が日常生活で何気なく利用しているものの多くは「有機化合物」である。中でも不斉炭素原子を有する光学活性な有機化合物は、特に医薬品において、その絶対配置の違いにより薬理作用が大きく異なる場合がある。従って、望みとする絶対配置を有する化合物を作り分ける「不斉合成法」は、その強力な供給手段となっている。代表者らは不斉合成に用いることが出来る、これまでに無い骨格を有する新しい不斉反応素子の開発を、本研究課題として進めてきた。種々検討した結果、代表者の開発した化学反応のみによって合成することが可能な新規骨格を有する不斉反応触媒を新たに開発し、不斉合成法に利用可能な新手法を提供することができた。

Report

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

    (16 results)

All 2019 2018 2017

All Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 8 results) Presentation (8 results) (of which Int'l Joint Research: 2 results,  Invited: 2 results)

  • [Journal Article] Facile Construction of an α-(1-Cyclopentenyl)ketone Core by Ruthenium-catalyzed Hydrative Cyclization of 1,6-Allenyne: Total Synthesis of (+)-Myomontanone2019

    • Author(s)
      Katagiri Koichi、Kodera Haruka、Tayu Masanori、Saito Nozomi
    • Journal Title

      Chemistry Letters

      Volume: 48 Issue: 8 Pages: 768-770

    • DOI

      10.1246/cl.190202

    • NAID

      130007687664

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel Nanoparticle-catalyzed Carboxylation of Unsaturated Hydrocarbon with CO2 Using Sulfur-modified Au-supported Nickel Material2019

    • Author(s)
      Taniguchi Takahisa、Saito Nozomi、Doi Ryohei、Kimoto Arato、Hoshiya Naoyuki、Fujiki Katsumasa、Shuto Satoshi、Fujioka Hiromichi、Arisawa Mitsuhiro、Sato Yoshihiro
    • Journal Title

      Chemistry Letters

      Volume: 48 Issue: 11 Pages: 1406-1409

    • DOI

      10.1246/cl.190650

    • NAID

      130007741839

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Transition Metal-Mediated Transformation of Ynamides and Application to Organic Synthesis2018

    • Author(s)
      齋藤 望、佐藤 美洋
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 76 Issue: 7 Pages: 699-709

    • DOI

      10.5059/yukigoseikyokaishi.76.699

    • NAID

      130007403452

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2018-07-01
    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed [2 + 2] Cyclization of 1,7-Allenynes in Ionic Liquid and Catalyst Recycling"2018

    • Author(s)
      Nozomi Saito, Momoko Koyama, Yoshihiro Sato
    • Journal Title

      Heterocycles

      Volume: 97 Issue: 2 Pages: 696-701

    • DOI

      10.3987/com-18-s(t)46

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Hydrocarboxylation of Ynamides with CO2 and H2O: An Observation of Unexpected Regioselectivity2017

    • Author(s)
      Ryohei Doi, Iman Abdullah, Takahisa Taniguchi, Nozomi Saito, Yoshihiro Sato
    • Journal Title

      Chemical Communications

      Volume: 53 Issue: 55 Pages: 7720-7723

    • DOI

      10.1039/c7cc03127k

    • NAID

      120006488397

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ligand-free Suzuki?Miyaura coupling using ruthenium(0) nanoparticles and a continuously irradiating microwave system2017

    • Author(s)
      Akiyama Toshiki、Taniguchi Takahisa、Saito Nozomi、Doi Ryohei、Honma Tetsuo、Tamenori Yusuke、Ohki Yuuta、Takahashi Naoyuki、Fujioka Hiromichi、Sato Yoshihiro、Arisawa Mitsuhiro
    • Journal Title

      Green Chemistry

      Volume: 19 Issue: 14 Pages: 3357-3369

    • DOI

      10.1039/c7gc01166k

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Direct C2-Functionalization of Indoles Triggered by the Generation of Iminium Species from Indole and Sulfonium Salt2017

    • Author(s)
      Masanori Tayu, Kazuya Nomura, Koki Kawachi, Kazuhiro Higuchi, Nozomi Saito, Tomomi Kawasaki
    • Journal Title

      Chem. Eur. J.

      Volume: 23 Issue: 45 Pages: 10925-10930

    • DOI

      10.1002/chem.201702338

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (+)-Gliocladin C Based on One-Pot Construction of a 3a-(3-Indolyl)pyrroloindoline Skeleton by Sulfonium-Mediated Cross-Coupling of Tryptophan and Indole2017

    • Author(s)
      Tayu, M.; Hui, Y.; Takeda, S.; Higuchi, K.; Saito, N.; Kawasaki, T
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 24 Pages: 6582-6585

    • DOI

      10.1021/acs.orglett.7b03293

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] Ruthenium(II)-Catalyzed Hydrative Cyclization of 1,6-Allenyne Leading to 1-Acylcylopentene Skeleton: Total Synthesis of (+)-Myomontanone2019

    • Author(s)
      齋藤望
    • Organizer
      ICPAC Yangon 2019
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 片桐光一、小寺遥夏、田湯正法、齋藤 望2019

    • Author(s)
      ルテニウム触媒による1,6-アレンインの水和を伴う環化反応を用いたα-(1-シクロペンテニル)ケトン骨格の構築
    • Organizer
      第139回薬学会年会
    • Related Report
      2018 Research-status Report
  • [Presentation] イナミドを用いたメタルビニリデン中間体を経由するインドール骨格の新規構築法2019

    • Author(s)
      五十木聡史、田湯正法、齋藤 望
    • Organizer
      第139回薬学会年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ルテニウム触媒を用いた1,6-アレンインの水の付加を伴う環化反応による(+)-myomontanoneの全合成2018

    • Author(s)
      片桐光一、小寺遥夏、田湯正法、齋藤 望
    • Organizer
      第48回複素環化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] "銅触媒を用いたイナミドの位置選択的カルボ亜鉛化によるエナミドの合成法:β3-アミノ酸の不斉合成へ向け て"2018

    • Author(s)
      松井寿雅子、尾形美咲、田湯正法、齋藤望
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] "ジアステレオ選択的ピロロインドリン骨格ワンポット構築反応の開発と(+)–gliocladin C合成研究への応用"2017

    • Author(s)
      回 芸、田湯正法、武田詩織、樋口和宏、齋藤 望、川﨑知己
    • Organizer
      第73回有機合成化学協会関東支部シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] "スルホニウム種によるピロロインドリンワンポット合成法を 利用した(+)-gliocladin C の不斉全合成"2017

    • Author(s)
      回 芸、田湯正法、武田詩織、樋口和宏、齋藤 望、川﨑知己
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] "Molecular Transformation of Polarized Alkynes ~Ni(0)-Promoted Carboxylation of Ynol Ethers and Ynamides~"2017

    • Author(s)
      Nozomi Saito
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC2017)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited

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

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