論文 2018


Metal-Free Transesterification Catalyzed by Tetramethylammonium Methyl Carbonate

Manabu Hatano, Yuji Tabata, Yurika Yoshida, Kohei Toh, Kenji Yamashita, Yoshihiro Ogura, and  Kazuaki Ishihara*

Green Chem. 2018, Just accepted.

The article was received on 26 Dec 2017, accepted on 13 Feb 2018 and first published on 13 Feb 2018.

Environmentally benign metal-free tetramethylammonium methyl carbonate is effective as a catalyst for the chemoselective, scalable, and reusable transesterification of various esters and alcohols in common organic solvents. In situ-generated highly active species, tetramethylammonium alkoxides, can greatly avoid the self-decomposition at ≤110 °C, and reusable. In particular, chelating substrates, such as amino alcohols, diols, triols, sugar derivatives, alkaloids, α-amino acid esters, etc., which deactivate conventional metal salt catalysts, can be used. A 100 gram scale biodiesel production was also demonstrated.

Enantioselective Aza-Friedel-Crafts Reaction of Indoles with Ketimines Catalyzed by Chiral Potassium Binaphthyldisulfonates

Manabu Hatano, Takuya Mochizuki, Keisuke Nishikawa, Kazuaki Ishihara*
ACS Catal. 2018, 8, 349–353.
Publication Date (Web): December 4, 2017 (Letter)

The enantioselective aza-Friedel–Crafts reaction of indoles with low-reactive ketimines has been developed in the presence of a chiral monopotassium binaphthyldisulfonate as a strong Brønsted acid catalyst. A broad substrate scope was achieved, and the corresponding 3-indolylmethanamines with a chiral quaternary carbon center were obtained in high yields with high enantioselectivities. The addition of a catalytic amount of acetic acid considerably promoted the reaction, and a gram-scale reaction could be achieved with reduced catalyst loading.

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ISHIHARA GROUP

名古屋大学

大学院工学研究科 有機・高分子化学専攻(工学部 化学生命工学科)
有機化学講座

触媒有機合成学研究グループ

〒464-8603 名古屋市千種区不老町

B2-3(611)

 

Laboratory of Catalysis in Organic Synthesis, Research Group of Molecular Chemistry, Graduate Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering (Undergraduate Department of Chemistry and Biotechnology, School of Engineering), Nagoya University

B2-3(611), Furo-cho, Chikusa, Nagoya 464-8603, Japan