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Development of Asymmetric Organic Catalysts Using Accurate and Efficient Conformational Analysis

Research Project

Project/Area Number 18H01969
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionFukuoka Institute of Technology

Principal Investigator

Kamachi Takashi  福岡工業大学, 工学部, 教授 (40403951)

Co-Investigator(Kenkyū-buntansha) 山本 英治  九州大学, 理学研究院, 助教 (70782944)
Project Period (FY) 2018-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥17,160,000 (Direct Cost: ¥13,200,000、Indirect Cost: ¥3,960,000)
Fiscal Year 2022: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2021: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2020: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2019: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2018: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Keywords有機分子触媒 / 配座解析 / 密度汎関数法 / 不斉合成
Outline of Final Research Achievements

Organocatalysts are ideal catalysts that are free from toxic heavy metal residues and can address the issues of rising rare metal prices and depletion. In this study, we have developed a variety of conformational analysis methods to elucidate the causes of enantioselectivity of organocatalysts. We used our own ConFinder program to perform fast and accurate conformational analysis. This program allows us to elucidate the specific conformations responsible for the high selectivity, providing hints for the analysis of reaction mechanisms and the design of catalysts. In collaboration with an experimental group developing organocatalysts, we conducted research on asymmetric hydrolysis reactions of esters.

Academic Significance and Societal Importance of the Research Achievements

従来利用されている金属を含む触媒は,貴金属が必要であったり,重金属を含むために環境汚染の問題がある.金属を含まない有機分子触媒に置き換えることができれば,これらの問題を解決することができるため,医薬品の合成やコスト削減が期待できる.最近,有機分子触媒の開発者がノーベル賞を受賞するなど,注目が高まっている.しかしながら,有機分子触媒と基質はの水素結合などの弱い相互作用で結びついており,その開発やメカニズム解明は実験的な手法だけでは難しい.本研究で用いている高精度な配座解析が有機分子触媒による不斉合成反応に有効であることを示すことができた.

Report

(6 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Annual Research Report
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (23 results)

All 2023 2022 2021 2020 2019 2018

All Journal Article (14 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 14 results,  Open Access: 2 results) Presentation (9 results) (of which Invited: 2 results)

  • [Journal Article] Theoretical Mechanistic Investigation of the Dynamic Kinetic Resolution of N-Protected Amino Acid Esters using Phase-Transfer Catalysts2023

    • Author(s)
      Yamamoto Eiji、Kobayashi Kaoru、Wakafuji Kodai、Kamachi Takashi、Tokunaga Makoto
    • Journal Title

      The Journal of Organic Chemistry

      Volume: - Issue: 12 Pages: 7748-7754

    • DOI

      10.1021/acs.joc.2c02352

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Systematical study on the electronic properties of monoazaphenanthrene compounds by theoretical calculations and experimental observations2022

    • Author(s)
      Hamamoto Nobutsugu、Yamashita Rika、Arae Sachie、Irie Ryo、Kamachi Takashi、Fujimoto Hitoshi
    • Journal Title

      Chemical Physics

      Volume: 552 Pages: 111370-111370

    • DOI

      10.1016/j.chemphys.2021.111370

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effect of Oxygen Vacancies on Adsorption of Small Molecules on Anatase and Rutile TiO<sub>2</sub> Surfaces: A Frontier Orbital Approach2021

    • Author(s)
      Hamamoto Nobutsugu、Tatsumi Toshinobu、Takao Motoshi、Toyao Takashi、Hinuma Yoyo、Shimizu Ken-ichi、Kamachi Takashi
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 125 Issue: 7 Pages: 3827-3844

    • DOI

      10.1021/acs.jpcc.0c09614

    • Related Report
      2021 Annual Research Report 2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Factors determining surface oxygen vacancy formation energy in ternary spinel structure oxides with zinc2021

    • Author(s)
      Hinuma Yoyo、Mine Shinya、Toyao Takashi、Kamachi Takashi、Shimizu Ken-ichi
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 23 Issue: 41 Pages: 23768-23777

    • DOI

      10.1039/d1cp03657b

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dynamic Kinetic Resolution of Azlactones via Phase-Transfer Catalytic Alcoholysis2021

    • Author(s)
      Wakafuji Kodai、Iwasa Satsuki、Ouchida Kina N.、Cho Hyemin、Dohi Hirotsugu、Yamamoto Eiji、Kamachi Takashi、Tokunaga Makoto
    • Journal Title

      ACS Catalysis

      Volume: 11 Issue: 22 Pages: 14067-14075

    • DOI

      10.1021/acscatal.1c03076

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Auto-Generation of Corrugated Nonpolar Stoichiometric Slab Models2020

    • Author(s)
      Hinuma Yoyo、Kamachi Takashi、Hamamoto Nobutsugu
    • Journal Title

      MATERIALS TRANSACTIONS

      Volume: 61 Issue: 1 Pages: 78-87

    • DOI

      10.2320/matertrans.MT-M2019215

    • NAID

      130007772455

    • ISSN
      1345-9678, 1347-5320
    • Year and Date
      2020-01-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Surface Oxygen Vacancy Formation Energy Calculations in 34 Orientations of β-Ga2O3 and θ-Al2O32020

    • Author(s)
      Hinuma Yoyo、Kamachi Takashi、Hamamoto Nobutsugu、Takao Motoshi、Toyao Takashi、Shimizu Ken-ichi
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 124 Issue: 19 Pages: 10509-10522

    • DOI

      10.1021/acs.jpcc.0c00994

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Frontier molecular orbital based analysis of solid-adsorbate interactions over group 13 metal oxide surfaces2020

    • Author(s)
      Liu C, Li Y, Takao M, Toyao T, Kamachi T, Hinuma Y, Takigawa I, Shimizu K
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 124(28) Issue: 28 Pages: 15355-65

    • DOI

      10.1021/acs.jpcc.0c04480

    • NAID

      120007116482

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Changes in Surface Oxygen Vacancy Formation Energy at Metal/Oxide Perimeter Sites: A Systematic Study on Metal Nanoparticles Deposited on an In2O3(111) Support2020

    • Author(s)
      Hinuma Yoyo、Toyao Takashi、Hamamoto Nobutsugu、Takao Motoshi、Shimizu Ken-ichi、Kamachi Takashi
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 124 Issue: 50 Pages: 27621-27630

    • DOI

      10.1021/acs.jpcc.0c10010

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Linear Correlations between Adsorption Energies and HOMO Levels for the Adsorption of Small Molecules on TiO2 Surfaces2019

    • Author(s)
      Kamachi Takashi、Tatsumi Toshinobu、Toyao Takashi、Hinuma Yoyo、Maeno Zen、Takakusagi Satoru、Furukawa Shinya、Takigawa Ichigaku、Shimizu Ken-ichi
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 123 Issue: 34 Pages: 20988-20997

    • DOI

      10.1021/acs.jpcc.9b05707

    • NAID

      120006882088

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Machine Learning for Catalysis Informatics: Recent Applications and Prospects2019

    • Author(s)
      Toyao Takashi、Maeno Zen、Takakusagi Satoru、Kamachi Takashi、Takigawa Ichigaku、Shimizu Ken-ichi
    • Journal Title

      ACS Catalysis

      Volume: 10 Issue: 3 Pages: 2260-2297

    • DOI

      10.1021/acscatal.9b04186

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Combined theoretical and experimental study on alcoholysis of amides on CeO 2 surface: A catalytic interplay between Lewis acid and base sites2018

    • Author(s)
      Kamachi Takashi、Siddiki S.M.A. Hakim、Morita Yoshitsugu、Rashed Md. Nurnobi、Kon Kenichi、Toyao Takashi、Shimizu Ken-ichi、Yoshizawa Kazunari
    • Journal Title

      Catalysis Today

      Volume: 303 Pages: 256-262

    • DOI

      10.1016/j.cattod.2017.09.006

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis2018

    • Author(s)
      Yamamoto Eiji、Wakafuji Kodai、Furutachi Yuho、Kobayashi Kaoru、Kamachi Takashi、Tokunaga Makoto
    • Journal Title

      ACS Catalysis

      Volume: 8 Issue: 7 Pages: 5708-5713

    • DOI

      10.1021/acscatal.8b00693

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Density Functional Theory Calculations of Oxygen Vacancy Formation and Subsequent Molecular Adsorption on Oxide Surfaces2018

    • Author(s)
      Hinuma Yoyo、Toyao Takashi、Kamachi Takashi、Maeno Zen、Takakusagi Satoru、Furukawa Shinya、Takigawa Ichigaku、Shimizu Ken-ichi
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 122 Issue: 51 Pages: 29435-29444

    • DOI

      10.1021/acs.jpcc.8b11279

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Presentation] 高効率的な均一系・不均一系触媒反応の開発2022

    • Author(s)
      山本英治
    • Organizer
      2022年度第2回有機合成化学講演会
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] 相間移動触媒によるアズラクトン類の不斉加アルコール分解反応2022

    • Author(s)
      岩佐 颯起・若藤 空大・大内田 希奈・山本 英治・蒲池 高志・徳永 信
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] キラル相間移動触媒を用いた不斉アルコリシスによるアズラクトン類の動的速度論分割2021

    • Author(s)
      若藤空大・岩佐颯起・大内田 希奈・チョヘミン・土肥弘嗣・山本英治・蒲池高志・徳永 信
    • Organizer
      第11回化学フェスタ
    • Related Report
      2021 Annual Research Report
  • [Presentation] 相間移動触媒を用いた不斉加アルコール分解によるアズラクトン類の動的速度 論的光学分割2020

    • Author(s)
      若藤空大・土肥弘嗣・チョヘミン・蒲池高志・山本英治・徳永信
    • Organizer
      第117回有機合成シンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] メタン活性化を目指した触媒インフォマティクスの展開2019

    • Author(s)
      蒲池高志、斉藤雅史、辻雄太、吉田将隆、吉澤一成
    • Organizer
      第124回触媒討論会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] TiO2表面における分子吸着のフロンティア軌道理論2019

    • Author(s)
      蒲池高志、巽俊暢、鳥屋尾隆、日沼洋陽、前野禅、高草木達、古川森也、瀧川一学、清水研一
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Bifunctional Phosphonium/Thiourea Salts as Phase-Transfer Catalysts: Enantioselective Protonation of Alkenyl Esters2019

    • Author(s)
      Kodai Wakafuji, Yusuke Mori, Gaku Teshima, Yuki Hidani, Eiji Yamamoto, and Makoto Tokunaga
    • Organizer
      24th Joint symposium between KB-CSJ and BB-KCS
    • Related Report
      2019 Annual Research Report
  • [Presentation] Phase-Transfer Catalytic Dynamic Kinetic Resolution of Amino Acid Esters with Water and Alcohols as Nucleophiles2019

    • Author(s)
      Kodai Wakafuji, Kaoru Kobayashi, Hyemin Cho, Hirotsugu Dohi, Takashi Kamachi, Eiji Yamamoto, Makoto Tokunaga
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 1,2,3,4,5-ペンタカルボキシシクロペンタジエン(PCCP)による不斉Mannich反応の理論的研究2018

    • Author(s)
      蒲池高志、斉藤雅史、吉澤一成
    • Organizer
      分子科学討論会
    • Related Report
      2018 Annual Research Report

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Published: 2018-04-23   Modified: 2024-01-30  

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