Research group of catalysis
TalTech priority area
Research classification (Frascati)
Head of the research group
Research group member
Doctoral students
Keyword
asymmetric synthesis
organocatalysis
cascade reactions
halogen-bond catalysis
enzymatic catalysis
oligosacharides
Overview
The main research object of the group is asymmetric organic synthesis. The research includesa total synthesis of bioactive compounds and specific investigations of cascade and catalytic reactions. Studies of asymmetric organocatalytic reactions are of importance. Aminocatalysis basedon covalently bound compounds, hydrogen-bondand halogen-bond catalysis based on noncovalentinteractions, enzymatic and co-operative catalysis are the main topics. Several reactions underthe study are cascade reactions providing severalnew chemical bonds in one step. It increasesatom-efficiency, decreases the number of stepsneeded and makes the whole process environmentally more benign (the number of work-upsteps and amount of solvent is diminished). Thesynthesis is supported by spectroscopic andcrystallographic experiments, chromatographyand quantum chemical calculations.The characteristic feature of the research is theapplication of the principles of sustainable andgreen chemistry in asymmetric synthesis.
Related department
Department of chemistry and biotechnology
Publications related to the research group
- Sihtmäe, M., Silm, E., Kriis, K., Kahru, A., Kanger, T. Aminocatalysts are more environmentally friendly than hydrogen-bonding catalysts // ChemSusChem (2022) vol. 15, 16, art. e202201045, 5 p. : ill.
https://doi.org/10.1002/cssc.202201045 - Hunt, K. E., Garcia-Sosa, A. T., Shalima, T., Maran, U., Vilu, R., Kanger, T. Synthesis of 6′-galactosyllactose, a deviant human milk oligosaccharide, with the aid of Candida antarctica lipase-B // Organic & biomolecular chemistry (2022) vol. 20, p. 4724–4735.
https://doi.org/10.1039/D2OB00550F - Kaasik, M., Martõnova, J., Erkman, K., Metsala, A., Järving, I., Kanger, T. Enantioselective Michael addition to vinyl phosphonates via hydrogen bond-enhanced halogen bond catalysis // Chemical science (2021) vol. 12, 21, p. 7561-7568.
https://doi.org/10.1039/D1SC01029H - Murre, A., Erkman, K., Järving, I., Kanger, T. Asymmetric chemoenzymatic one-pot synthesis of α-Hydroxy half-esters // ACS Omega (2021) vol. 6, 31, p. 20686-20698 : ill.
https://doi.org/10.1021/acsomega.1c02973 - Kimm, M., Järving, I., Ošeka, M., Kanger, T. Asymmetric organocatalytic [2,3]-Wittig rearrangement of cyclohexanone derivatives // European journal of organic chemistry (2021) 21, p. 3113−3120 : ill.
https://doi.org/10.1002/ejoc.202100435 - Trubitsõn, D., Martõnova, J., Kudrjašova, M., Erkman, K., Järving, I., Kanger T. Enantioselective organocatalytic Michael addition to unsaturated indolyl ketones // Organic letters (2021) vol. 23, 5, p. 1820-1824.
https://doi.org/10.1021/acs.orglett.1c00222 - Spinnato, D., Schweitzer-Chaput, B., Goti, G., Ošeka, M., Melchiorre, P A photochemical organocatalytic strategy for the α-alkylation of ketones by using radicals // Angewandte Chemie international Edition (2020) Vol. 59, 24, p. 9485 - 9490.
https://doi.org/10.1002/anie.201915814 - Ošeka, M., Laudadio, G., van Leest, N., Dyga, M., Bartolomeu, A. de A., Gooßen, L.J., de Bruin, B., de Oliveira, K.T., Noël, T. Electrochemical aziridination of internal alkenes with primary amines // Chem (2021) Vol. 7, Issue 1, p. 255 - 266.
https://doi.org/10.1016/j.chempr.2020.12.002 - Kaasik, M., Kanger, T. Supramolecular halogen bonds in asymmetric catalysis // Frontiers in chemistry (2020) vol. 8, art. 599064, 18 p. : ill.
https://doi.org/10.3389/fchem.2020.599064 - Trubitsõn, D., Kanger, T. Enantioselective Catalytic Synthesis of N-alkylated Indoles // Symmetry (2020) vol. 12, 7, art. 1184 ; 30 p.: ill.
https://doi.org/10.3390/sym12071184 - Trubitsõn, D., Martõnova, J., Erkman, K., Metsala, A., Saame, J., Kõster, K., Järving, I., Leito, I., Kanger, T. Enantioselective N-Alkylation of Nitroindoles under Phase-Transfer Catalysis // Synthesis (2020) vol. 52, 7, p. 1047-1059.
https://doi.org/10.1055/s-0039-1690751 - Ivanova, L., Rausalu, K., Ošeka, M., Kananovich, D. G., Žusinaite, E., Tammiku-Taul, J., Lopp, M., Merits, A., Karelson, M. Novel analogues of the Chikungunya virus protease inhibitor: molecular design, synthesis, and biological evaluation // ACS omega (2021) vol. 6, 16, p. 10884–10896.
https://doi.org/10.1021/acsomega.1c00625 - Kooli, A., Wesenberg, L., Beslać, M., Krech, A., Lopp, M., Noël, T., Ošeka, M. Electrochemical hydroxylation of electron-rich arenes in continuous flow // European journal of organic chemistry (2022) vol. 2022, 20, art. e202200540.
https://doi.org/10.1002/ejoc.202200011 - Kõllo, M., Kasari, M., Kasari, V., Pehk, T., Järving, I., Lopp, M., Jõers, A., Kanger, T. Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols // Beilstein journal of organic chemistry (2021) vol. 17, p. 581–588.
https://doi.org/10.3762/bjoc.17.52 - Kriis, K., Martõnov, H., Miller, A., Erkman, K., Järving, I., Kaasik, M., Kanger, T. Multifunctional catalysts in the asymmetric Mannich reaction of malononitrile with N-Phosphinoylimines : coactivation by halogen bonding versus hydrogen bonding // The journal of organic chemistry (2022) vol. 87, 11, p. 7422-7435 : ill.
https://doi.org/10.1021/acs.joc.2c00674 - Silm, E., Järving, I., Kanger, T. Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole // Beilstein Journal of Organic Chemistry (2022) vol. 18, p. 167-173.
https://doi.org/10.3762/bjoc.18.18 - Murre, A., Erkman, K., Kaabel, S., Järving, I., Kanger, T. Diastereoselective [2,3]-sigmatropic rearrangement of N-allyl ammonium ylides // Synthesis (2019) vol. 51, 22, p. 4183–4197.
https://doi.org/10.1055/s-0039-1690185 - Silm, E., Kaabel, S., Järving, I., Kanger, T. Asymmetric organocatalytic Michael addition–cyclisation cascade of cyclopentane-1,2-dione with alkylidene malononitriles // Synthesis (2019) vol. 51, 22, p. 4198-4204.
https://doi.org/10.1055/s-0039-1690484 - Reitel, K., Kriis, K., Järvin, I., Kanger, T. Study of the asymmetric organocatalyzed [3+2] annulation of cyclopropenone and β-keto ester // Chemistry of heterocyclic compounds (2018) vol. 54, 10, p. 929–933 : ill.
https://doi.org/10.1007/s10593-018-2372-1 - Kimm, M., Ošeka, M., Kaabel, S., Metsala, A., Järving, I., Kanger, T. [2,3]-Wittig rearrangement as a formal asymmetric alkylation of α-branched ketones // Organic letters (2019) vol. 21, 13, p. 4976-4980.
https://doi.org/10.1021/acs.orglett.9b01495 - Trubitsõn, D., Žari, S., Kaabel, S., Kudrjashova, M., Kriis, K., Järving, I., Pehk, T., Kanger, T. Asymmetric organocatalytic cascade synthesis of tetrahydrofuranyl spirooxindoles // Synthesis (2018) vol. 50, 2, p. 314-322 : ill.
https://doi.org/10.1055/s-0036-1590918 - Peterson, A., Kaasik, M., Metsala, A., Järving, I., Adamson, J., Kanger, T. Tunable chiral triazole-based halogen bond donors : assessment of donor strength in solution with nitrogen-containing acceptors // RSC advances (2019) vol. 9, 21, p. 11718–11721 : ill.
https://doi.org/10.1039/c9ra01692a - Kaasik, M., Kaabel, S., Kriis, K., Järving, I., Kanger, T. Synthesis of chiral triazole-based halogen bond donors // Synthesis (2019) vol. 51, 10, p. 2128-2135 : ill.
https://doi.org/10.1055/s-0037-1610864 - Kaasik, M., Metsala, A., Kaabel, S., Kriis, K., Järving, I., Kanger, T. Halo-1,2,3-triazolium salts as halogen bond donors for the activation of imines in dihydropyridinone synthesis // Journal of organic chemistry (2019) vol. 84, 7, p. 4294–4303 : ill.
https://doi.org/10.1021/acs.joc.9b00248 - Iskryk, M., Barysevich, M., Ošeka, M., Adamson, J., Kananovich, D. Asymmetric Kulinkovich hydroxycyclopropanation of alkenes mediated by titanium(IV) TADDOLate complexes // Synthesis (2019) vol. 51, 9, p. 1935-1948 : ill.
https://doi.org/10.1055/s-0037-1611709 - Ramkumar, N., Plantus, K., Ozola, M., Mishnev, A., Nikolajeva, V., Senkovs, M., Ošeka, M., Veliks, J. Photoredox-catalyzed direct C–H monofluoromethylation of heteroarenes // New journal of chemistry (2023) vol. 47, 44, p. 20642-20652.
https://doi.org/10.1039/D3NJ04313D - Murre, A., Mikli, V., Erkman, K., Kanger, T. Primary amines as heterogeneous catalysts in an enantioselective [2,3]-Wittig rearrangement reaction // iScience (2023) vol. 26, 10, art. 107822, 18 p. : ill.
https://doi.org/10.1016/j.isci.2023.107822 - Kaasik, M., Kanger, T. Halogen-Bonding Organocatalysis - New Opportunities for Asymmetric Synthesis // Asymmetric Organocatalysis: New Strategies, Catalysts, and Opportunities. Vol. 1. Weinheim : Wiley, 2022. p. 203-224.
https://doi.org/10.1002/9783527832217.ch6