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Synthetic Medicinal Chemistry(Chemistry)

Kanomata KyoheiAssistant professor

2010 B.Sc. Department of Engineering, Soka University
2012 M.Sc. Graduate Scholl of Science, Tohoku University
2015 Ph.D. Graduate Scholl of Science, Tohoku University
2015–2016 Postdoctoral researcher, Kyoto University
2016–2020 Postdoctoral researcher/JSPS Research Fellow, Kyushu University
2021 Special Postdoctoral Researcher (SPDR), RIKEN
2021 Assistant Professor, Graduate School of Pharmaceuticals, Osaka University

Research theme

Asymmetric organocatalysis

Asymmetric synthesis of biologically active compounds using organocatalysts are attracting more and more attention in these days because of their environmentally benign nature. Our current research topic includes developing novel asymmetric reactions using organocatalysts, as well as analyzing these reactions using quantum chemical calculations and developing a prediction system using machine learning.

Catalysis of cellulose nanofibers

Proline, one of the natural amino acids, functions as an organocatalyst, promoting important bond-forming reactions such as the aldol reaction. Although proline is an inexpensive and harmless, it suffered from poor activity and instability. We recently have discovered that cellulose nanofibers can promote proline catalysis and improve selectivity. We are now conducting research to elucidate the mechanism of this interesting phenomenon and to apply it to various catalytic reactions.

Pickering emulsion catalysis

Amphiphilic nanoparticles are known to exhibit emulsifying properties as surfactants. We are focusing on this phenomenon and developing new production processes for pharmaceutical compounds by integrating organocatalysis and enzymatic reaction technologies.

Representative achievements

Chemo- and regioselective cross-dehydrogenative coupling reaction of 3-hydroxycarbazoles with arenols catalyzed by a mesoporous silica-supported oxovanadium
K. Kasama, K. Kanomata, Y. Hinami, K. Mizuno, Y. Uetake, T. Amaya, M. Sako, S. Takizawa, H. Sasai, S. Akai
RSC Advances, 11, 35342–35350 (2021).

Direct nucleophilic substitution of alcohols using an immobilized oxovanadium catalyst
T. Nishio, S. Yoshioka, K. Hasegawa, K. Yahata, K. Kanomata, S. Akai
European Journal of Organic Chemistry, 31, 4417–4422 (2021).

Four-step one-pot catalytic asymmetric synthesis of polysubstituted tricyclic compounds: lipase-catalyzed dynamic kinetic resolution followed by an intramolecular Diels–Alder reaction
I. Tsuchimochi, S. Hori, Y. Takeuchi, M. Egi, T. Satoh, K. Kanomata, T. Ikawa, S. Akai
Synlett, 32, 822–828 (2021).

Nanocellulose enriches enantiomers in asymmetric aldol reactions
R. J. Ranaivoarimanana, X. Habaki, T. Uto, K. Kanomata, T. Yui, T. Kitaoka
RSC Advances, 10, 37064–37071 (2020).

Chitosan nanofiber-catalyzed highly selective Knoevenagel condensation in aqueous methanol
Y. Hirayama, K. Kanomata, M. Hatakeyama, T. Kitaoka
RSC Advances, 10, 26771–26776 (2020).

Lignin-inspired surface modification of nanocellulose by enzyme-catalyzed radical coupling of coniferyl alcohol in Pickering emulsion
K. Kanomata, N. Fukuda, T. Miyata, P. Y. Lam, T. Takano, Y. Tobimatsu, T. Kitaoka
ACS Sustainable Chemistry & Engineering, 8, 1185–1194 (2020).

Mechanism and origin of stereoselectivity in chiral phosphoric acid-catalyzed aldol-type reactions of azlactones with vinyl ethers
K. Kanomata, Y. Nagasawa, Y. Shibata, M. Yamanaka, F. Egawa, J. Kikuchi, M. Terada
Chemistry – A European Journal, 26, 3364–3372 (2020).

Cooperative catalysis of cellulose nanofiber and organocatalyst in direct aldol reactions
K. Kanomata, N. Tatebayashi, X. Habaki, T. Kitaoka
Scientific Reports, 8:4098, 1–6 (2018).

Study of stereocontrolling elements in chiral phosphoric acid catalyzed addition reaction of vinylindoles with azlactones
K. Kanomata, M. Terada
Synlett, 27, 581–585 (2016).

Secondary stereocontrolling interactions in chiral Brønsted acid catalysis: study of a Petasis-Ferrier-type rearrangement catalyzed by chiral phosphoric acids
K. Kanomata, Y. Toda, Y. Shibata, M. Yamanaka, S. Tsuzuki, I. D. Gridnev, M. Terada
Chemical Science, 5, 3515–3523 (2014).