Kyushu University Academic Staff Educational and Research Activities Database
List of Papers
Yamamoto Eiji Last modified date:2022.06.14

Assistant Professor / Multidisciplinary Chemistry / Department of Chemistry / Faculty of Sciences


Papers
1. Kodai Wakafuji, Satsuki Iwasa, Kina N. Ouchida, Hyemin Cho, Hirotsugu Dohi, Eiji Yamamoto,* Takashi Kamachi, Makoto Tokunaga*, Dynamic Kinetic Resolution of Azlactones via Phase-Transfer Catalytic Alcoholysis, ACS Catalysis, https://doi.org/10.1021/acscatal.1c03076, 11, 22, 14067-14075, 2021.11, [URL].
2. Eiji Yamamoto,* Yasutaka Kawai, Kei Takakura, Moemi Kimura, Haruno Murayama, Hironobu Matsueda, Shujiro Otsuki, Hiroshi Sakata, Makoto Tokunaga*, Convenient Unsymmetrical Disulfane Synthesis: Basic Zeolite-Catalyzed Thiol-Disulfane Exchange Reaction, ChemCatChem, 13, 22, 4694-4699, 2021.09, [URL].
3. Zhenzhong Zhang,Tetsuya Mamba,Qi-An Huang,Haruno Murayama,Eiji Yamamoto,Tetsuo Honma,Makoto Tokunaga, The additive effect of amines on the dihydroxylation of buta-1,3-diene into butenediols by supported Pd catalysts., Molecular Catalysis, doi.org/10.1016/j.mcat.2019.110502, 475, 110502, 2019.10.
4. Zhenzhong Zhang,Tetsuya Mamba,Qi-An Huang, Haruno Murayama, Eiji Yamamoto,Tetsuo Honma, Makoto Tokunaga, The additive effect of amines on the dihydroxylation of buta-1,3-diene into butenediols by supported Pd catalysts, Molecular Catalysis, 10.1016/j.mcat.2019.110502, 2019.10, [URL].
5. 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..
6. 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].
7. Eiji Yamamoto, Satoshi Ukigai, Hajime Ito, Formal Nucleophilic Silyl Substitution of Aryl Halides with Silyllithium Reagents via Halogenophilic Attack of Silyl Nucleophiles, Synlett, 10.1055/s-0036-1590835, 28, 18, 2460-2464, 2017.11.
8. Eiji Yamamoto, Ryosuke Shishido, Tomohiro Seki, Hajime Ito, Tris(trimethylsilyl)silylboronate Esters
Novel Bulky, Air- and Moisture-Stable Silylboronate Ester Reagents for Boryl Substitution and Silaboration Reactions, Organometallics, 10.1021/acs.organomet.7b00476, 36, 16, 3019-3022, 2017.08.
9. Zhenzhong Zhang, Yuhya Kumamoto, Taishin Hashiguchi, Tetsuya Mamba, Haruno Murayama, Eiji Yamamoto, Tamao Ishida, Tetsuo Honma, Makoto Tokunaga, Wacker Oxidation of Terminal Alkenes Over ZrO2-Supported Pd Nanoparticles Under Acid- and Cocatalyst-Free Conditions, ChemSusChem, 10.1002/cssc.201701016, 10, 17, 3482-3489, 2017.08.
10. Manuel Orlandi, Margaret J. Hilton, Eiji Yamamoto, F. Dean Toste, Matthew S. Sigman, Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates, Journal of the American Chemical Society, 10.1021/jacs.7b06917, 139, 36, 12688-12695, 2017.09, A mechanistic study of the Pd-catalyzed enantioselective 1,1-diarylation of benzyl acrylates that is facilitated by a chiral anion phase transfer (CAPT) process is presented. Kinetic analysis, labeling, competition, and nonlinear effect experiments confirm the hypothesized general mechanism and reveal the role of the phosphate counterion in the CAPT catalysis. The phosphate was found to be involved in the phase transfer step and in the stereoinduction process, as expected, but also in the unproductive reaction that provides the traditional Heck byproduct. Multivariate correlations revealed the CAPT catalyst’s structural features, affecting the production of this undesired byproduct, as well as weak interactions responsible for enantioselectivity. Such putative interactions include π-stacking and a CH···O electrostatic attraction between the substrate benzyl moiety and the phosphate. Analysis of the computed density functional theory transition structures for the stereodetermining step of the reaction supports the multivariate model obtained. The presented work provides the first comprehensive study of the combined use of CAPT and transition metal catalysis, setting the foundation for future applications..
11. 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..
12. 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.
13. 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.
14. Hiroaki Iwamoto, Koji Kubota, Eiji Yamamoto, Hajime Ito, Copper(I)-Catalyzed Carbon–Halogen Bond-Selective Boryl Substitution of Alkyl Halides Bearing Terminal Alkene Moieties, Chemical Communication, 51, 9655-9658, 2015.05.
15. 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.
16. 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.
17. Koji Kubota, Iwamoto Hiroaki, Eiji Yamamoto, Hajime Ito, Silicon-Tethered Strategy for Copper(I)-Catalyzed Stereo- and Regioselective Alkylboration of Alkynes, Organic Letters, 17, 3, 620-623, 2015.01.
18. 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.
19. Koji Kubota, Eiji Yamamoto, Hajime Ito, Copper(I)-Catalyzed Enantioselective Nucleophilic Borylation of Aldehydes: an Efficient Route to Enantiomerically Enriched α-Alkoxyorganoboronate Esters, Journal of the American Chemical Society, 137, 1, 420-424, 2014.12.
20. Koji Kubota, Eiji Yamamoto, Hajime Ito, Copper(I)-Catalyzed Borylative Exo-Cyclization of Alkenyl Halides Containing Unactivated Double Bond, Journal of the American Chemical Society, 135, 7, 2635-2640, 2013.01.
21. Koji Kubota, Eiji Yamamoto, Hajime Ito, Regio- and Enantioselective Monoborylation of Alkenylsilanes Catalyzed by an Electron-Donating Chiral Phosphine–Copper(I) Complex, Advanced Synthesis & Catalysis, 355, 3527-3531, 2013.12.
22. 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.
23. Eiji Yamamoto, Yuko Horita, Hajime Ito, Potassium tert-butoxide-mediated regioselective silaboration of aromatic alkenes, Chemical Communication, 48, 8006-8008, 2012.06.
24. Young-Min Kim, Eiji Yamamoto, Min-Sun Kan, Hiroyuki Nakai, Wataru Saburi, Masayuki Okuyama, Haruhide Mori, Kazumi Funane, Mitsuru Momma, Zui Fujimoto, Mikihiko Kobayashi, Doman Kim, Atsuo Kimura, Bacteroides thetaiotaomicron VPI-5482 glycoside hydrolase family 66 homolog catalyzes dextranolytic and cyclization reactions, The FEBS Journal, 279, 17, 3185-3191, 2012.08.
25. 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.
26. Itoh Hisashi, Eiji Yamamoto, Shigeyuki Masaoka, Ken Sakai, Makoto Tokunaga, Kinetic resolution of P-chirogenic compounds by Pd-catalyzed alcoholysis of vinyl ethers, Advanced Synthesis & Catalysis, 351, 11/12, 1796-1800, 2009.07.
27. 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.
28. Takeshi Sakuma, Eiji Yamamoto, Hiroshi Aoyama, Yasushi Obora, Yasushi Tsuji, Makoto Tokunaga, Kinetic resolution of phosphoryl and sulfonyl esters of 1,1′-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers, Tetrahedron Asymmetry, 19, 13, 1593-1599, 2008.07.