九州大学-研究者情報 [山本英治 (准教授) 理学研究院化学部門]

1.	Eiji Yamamoto,Kaoru Kobayashi,Kodai Wakafuji,Takashi Kamachi,Makoto Tokunaga, Theoretical Mechanistic Investigation of the Dynamic Kinetic Resolution of N-Protected Amino Acid Esters using Phase-Transfer Catalysts, Journal of Organic Chemistry, https://doi.org/10.1021/acs.joc.2c02352, 2023.02, [URL], A detailed theoretical mechanistic investigation on the dynamic kinetic resolution of N-protected amino acid esters using phase-transfer catalysts is described. Semiautomatic exhaustive conformation search of transition state (TS)-like structures were carried out using the ConFinder program and the pseudo-TS conformational search (PTSCS) method. This conformational search method successfully provided reasonable TS structures for determining the stereoselectivity in the asymmetric base hydrolysis of hexafluoroisopropyl (HFIP) esters as well as the racemization mechanism. Furthermore, the independent gradient model (IGM) analysis of the TS structures suggested that the H-bonding interactions with the oxyanion hole and π-stacking interactions are the common important features of the proposed TS structures that determine the stereoselectivity..
2.	Yasutaka Kawai, Kazuki Haruguchi, Keisei Sumikawa, Mai Kawada, Eiji Yamamoto, Haruno Murayama, Makoto Tokunaga, Aerobic oxidation of isoprene glycol with platinum-bismuth nanoparticles catalysts supported on metal oxides, Applied Catalysis A: General, https://doi.org/10.1016/j.apcata.2022.118781, 643, 118781, 2022.08, [URL].
3.	Qi-An Huang, Takaaki Ikeda, Kazuki Haruguchi, Seiya Kawai, Eiji Yamamoto, Haruno Murayama, Tamao Ishida, Tetsuo Honma, Makoto Tokunaga, Intramolecular cyclization of alkynoic acid catalyzed by Na-salt-modified Au nanoparticles supported on metal oxides , Applied Catalysis A: General, https://doi.org/10.1016/j.apcata.2022.118765, 643, 118765, 2022.08, [URL].
4.	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].
5.	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].
6.	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..
7.	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].
8.	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..
9.	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.
10.	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.
11.	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.
12.	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.
13.	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.
14.	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.
15.	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.
16.	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.

主要総説, 論評, 解説, 書評, 報告書等

全てを見る→

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.
3.	山本英治, 徳永信, キラル四級アンモニウム塩を触媒とする不斉塩基加水分解反応の開発, 月刊ファインケミカル, 2014.06.

主要学会発表等

全てを見る→

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.

特許出願・取得

特許出願件数 3件

特許登録件数 0件

学会活動

所属学会名

触媒学会

日本化学会

有機合成化学協会

学会大会・会議・シンポジウム等における役割

2016.04.23～2016.04.23, 万有福岡シンポジウム, 運営補助.

2016.07.02～2016.07.02, 第53回化学関連支部合同九州大会, ポスター審査員.

学術論文等の審査

年度	外国語雑誌査読論文数	日本語雑誌査読論文数	国際会議録査読論文数	国内会議録査読論文数	合計
2017年度	1				1
2016年度					0

その他の研究活動

海外渡航状況, 海外での教育研究歴

ユタ大学, UnitedStatesofAmerica, 2015.02～2016.02.

受賞

有機合成化学協会九州山口支部奨励賞, 有機合成化学協会九州山口支部, 2022.06.

平成17年度クラーク賞, 北海道大学, 2005.03.

平成23年度有機合成化学協会九州山口支部ポスター賞, 有機合成化学協会九州山口支部, 2011.04.

ファインケミカルズ合成触媒国際会議2011“Oral Presentation”, 触媒学会, 2011.04.

院生プロジェクト優秀研究賞, 九州大学グローバルＣＯＥ, 2011.04.

平成24年Symposium on Molecular Chirality Asia 2012 ポスター賞, 分子不斉研究機構 MCRO, 2012.04.

日本化学会第93春季年会優秀講演賞（学術）, 日本化学会, 2013.04.

研究資金

科学研究費補助金の採択状況(文部科学省、日本学術振興会)

2020年度～2020年度, 基盤研究(C), 代表, 相間移動触媒を用いた立体選択的なエステル官能基変換反応の開発.

2018年度～2022年度, 基盤研究(B), 分担, 高速かつ高精度な配座解析を軸とした理論計算が先導する不斉有機触媒の開発.

2018年度～2019年度, 若手研究, 代表, アンモニウムヒドロキシド活性種の構造制御に基づく触媒的不斉加水分解反応の開発.

2016年度～2017年度, 研究活動スタート支援, 代表, 双性イオン型求核触媒活性種を活用するエステル不斉塩基加水分解反応の開発.

競争的資金(受託研究を含む)の採択状況

2019年度～2019年度, 2019年度豊田理研スカラー, 代表, 低反応性ジスルフィドを用いる効率的な非対称S-S結合形成反応開発と生理活性化合物合成への応用.

2016年度～2016年度, 平成２８年度 QRプログラム『わかばチャレンジ』, 代表, キラル四級アンモニウムアルコールを求核触媒とする不斉エステル加水分解反応の開発.

共同研究、受託研究(競争的資金を除く)の受入状況

2022.01～2023.01, 代表, 貴金属触媒を用いた酸化反応に関する研究.

2021.09～2022.08, 代表, 環状アセタールの水素化還元反応に関する研究.

2019.04～2023.03, 代表, (メタ)アクリルモノマー合成のための新規反応およびその触媒の探索.

九大関連コンテンツ

pure2017年10月2日から、「九州大学研究者情報」を補完するデータベースとして、Elsevier社の「Pure」による研究業績の公開を開始しました。

QIR　九州大学学術情報リポジトリシステム情報科学研究院

理学部・理学研究院


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