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Yamamoto Eiji Last modified date:2019.07.17

Assistant Professor / Multidisciplinary Chemistry
Department of Chemistry
Faculty of Sciences


Graduate School
Undergraduate School


Phone
092-802-4141
Academic Degree
Science
Field of Specialization
Organic Synthesis, Catalysis Chemistry
Outline Activities
Organic Synthesis、Asymmetric Synthesis、Catalysis
Research
Research Interests
  • Developing catalytic asymmetric reactions using oxygen nucleophiles、 Development of solid catalysts
    keyword : Asymmetric Synthesis、Phase-Transfer Catalyst、Supported Catalyst
    2016.03~2017.04.
Academic Activities
Reports
1. 山本 英治, Recent Trends of Asymmetric Catalysis with Water as a Nucleophile., 有機合成化学協会誌, 2012.10.
2. 山本 英治, 泉 清孝, 堀田 優子, 浮海 智, 伊藤 肇, Formal Nucleophilic Boryl Substitution of Organic Halides with Silylborane/Alkoxy Base System, Topics in Catalysis, 2014.04.
Papers
1. Eiji YamamotoKodai WakafujiYusukeMori GakuTeshimaYuki HidaniMakoto Tokunaga, Enantioselective Protonation of Enol Esters with Bifunctional Phosphonium/Thiourea Catalysts, Organic Letters, 10.1021/acs.orglett.9b01216, 21, 11, 4030-4034, 2019.05, [URL], Bifunctional phosphonium/thioureas derived from tert-leucine behaved as highly selective catalysts for enantioselective protonation of enol esters, providing α-chiral ketones in yields of up to 99% with high enantioselectivities (up to 98.5:1.5 er). Control experiments clarified that a bulky tert-butyl group and phosphonium and thiourea moieties were necessary to achieve such high stereoselectivity. In addition, mechanistic investigations indicated the catalyst was converted to the corresponding betaine species, which served as a monomolecular catalyst..
2. Eiji Yamamoto, Kodai Wakafuji, Yuho Furutachi, Kaoru Kobayashi, Takashi Kamachi, and Makoto Tokunaga, Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis, ACS Catalysis, 10.1021/acscatal.8b00693, 8, 5708-5713, 2018.05, [URL].
3. Eiji Yamamoto, Margaret J. Hilton, Manuel Orlandi, Vaneet Saini, F. Dean Toste, Matthew S. Sigman, Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer, Journal of the American Chemical Society, 10.1021/jacs.6b11367, 2016.11, Enantioselective 1,1-diarylation of terminal alkenes enabled by the combination of Pd catalysis with a chiral anion phase transfer (CAPT) strategy is reported herein. The reaction of substituted benzyl acrylates with aryldiazonium salts and arylboronic acids gave the corresponding 3,3-diarylpropanoates in moderate to good yields with high enantioselectivies (up to 98:2 er). Substituents on the benzyl acrylate and CAPT catalyst significantly affect the enantioselectivity, and multidimensional parametrization identified correlations suggesting structural origins for the high stereocontrol..
4. Eiji Yamamoto, Kiyotaka Izumi, Ryosuke Shishido, Tomohiro Seki, Noriaki Tokoda, Hajime Ito, Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane, Chemistry -A European Journal, 10.1002/chem.201604021, 22, 49, 17547-17551, 2016.08.
5. Eiji Yamamoto, Ryoto Kojima, Koji Kubota, Hajime Ito, Copper(I)-Catalyzed Diastereoselective Borylative Exo-Cyclization of Alkenyl Aryl Ketones, Synlett, 27, 272-276, 2015.11.
6. Ryohei Uematsu, Eiji Yamamoto, Satoshi Maeda, Hajime Ito, Tetsuya Taketsugu, Reaction Mechanism of the Anomalous Formal Nucleophilic Borylation of Organic Halides with Silylborane: Combined Theoretical and Experimental Studies, Journal of the American Chemical Society, 137, 12, 4090-4099, 2015.03.
7. Eiji Yamamoto, Satoshi Ukigai, Hajime Ito, Boryl Substitution of Functionalized Aryl-, Heteroaryl-, and Alkenyl Halides with Silylborane and Alkoxy Base: Expanded Scope and Mechanistic Studies, Chemical Science, 6, 2943-2951, 2015.03.
8. Eiji Yamamoto, Yuta Takenouchi, Taichi Ozaki, Takanori Miya, Hajime Ito, Copper(I)-Catalyzed Enantioselective Synthesis of α-Chiral Linear or Carbocyclic (E)-γ-Alkoxyallylboronates, Journal of the American Chemical Society, 136, 47, 16515-16521, 2014.10.
9. Eiji Yamamoto, Kiyotaka Izumi, Yuko Horita, Hajime Ito, Anomalous Reactivity of Silylborane: Transition-Metal-Free Boryl Substitution of Aryl, Alkenyl, and Alkyl Halides with Silylborane/Alkoxy Base Systems, Journal of the American Chemical Society, 134, 49, 19997-20000, 2012.11.
10. Eiji Yamamoto, Daichi Gokuden, Ayano Nagai, Takashi Kamachi, Kazunari Yoshizawa, Akiyuki Hamasaki, Tamao Ishida, Makoto Tokunaga, Hydrolytic Enantioselective Protonation of Cyclic Dienyl Esters and a b-diketone with Chiral Phase-transfer Catalysts., Organic Letters, 14, 24, 6178-6181, 2012.12.
11. Eiji Yamamoto, Ayano Nagai, Akiyuki Hamasaki, Makoto Tokunaga, Catalytic Asymmetric Hydrolysis: Asymmetric Hydrolytic Protonation of Enolesters Catalyzed by Phase Transfer Catalysts, Chemistry -A European Journal, 17, 26, 7178-7182, 2011.05.
Presentations
1. Gaku Teshima, Yusuke Mori, Yuki Hidani, Eiji Yamamoto, Makoto Tokunaga, Bifunctional Thiourea-Quaternary Phosphonium Salts Catalyzed Enantioselective Protonation of Alkenyl Esters, IRCCS-JST CREST Joint Symposium, 2018.01.
2. Kodai Wakafuji , Hyemin Cho, Takashi Kamachi, Eiji Yamamoto, Makoto Tokunaga , Phase-Transfer Catalyzed Asymmetric Alcoholysis of N-Protected Amino Acid Esters and Azlactones via Dynamic Kinetic Resolution, 6th Japan–UK Symposium on Asymmetric Catalysis, 2018.11.
3. Kodai Wakafuji, Yusuke Mori, Gaku Teshima, Yuki Hidani, Eiji Yamamoto, and Makoto Tokunaga, Bifunctional Phosphonium/Thiourea Salts as Phase-Transfer Catalysts: Enantioselective Protonation of Alkenyl Esters, 24th Joint symposium between KB-CSJ and BB-KCS, 2019.06.
4. Akiko Murakami, Eiji Yamamoto, Takuma Takehisa, Makoto Tokunaga. , Asymmetric Base Hydrolysis of 2–Arylpropanoic Acid Esters Catalyzed by Chiral Phase-Transfer Catalysts., C&FC2016, 2016.11.
Educational
Other Educational Activities
  • 2016.09.