Asymmetric oxidation
Research classification (Frascati)
Head of the research group
Research group member
Doctoral students
Keyword
asymmetric chemical analysis and catalysis
synthesis of bioactive and nature compounds
Overview
The research is closely related to the topic of theCenter of Excellence in Molecular Cell Technology (CEMCE).The research is mainly focused on the followingtopics: Selective alkylation of phenols and naphthols. Alkyl-substituted Li-phenolatesand naphtholates have been shown toreact with alkyl bromides in aqueous media to give o- and p-substituted phenolsand naphthols in an organic solvent toselectively give ortho-alkylated products.Alkylation of 1- and 2- naphthols in ananhydrous medium provides the optionalpossibility to obtain only one of the possible isomers. Synthesis of 9,11-secosterols. A 9,11-secosterol carbon skeleton was synthesizedfrom a natural sterol using transformationwith genetically engineered whole cells. Abreakthrough in developing a total synthesis scheme was achieved. The results arein publishing process. New advances of cyclopropane chemistry. Asummary of the enantioselective reactionsof chiral titanium-cyclopropane reagentsover the past 30 years were our researchers have a significant contribution.
Related department
Publications related to the research group
- 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., Rõuk, K., Lopp, M. Synthesis of 2-(S)-[(4-methylphenyl)sulfinyl]-2-cyclo penten-1-one, a D-ring precursor of 9,11-secosterols // Proceedings of the Estonian Academy of Sciences (2022) vol. 71, 4, p. 307-313 : ill.
https://doi.org/10.3176/proc.2022.4.01 - 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 - Kananovich, D., Elek, G. Z., Lopp, M., Borovkov, V. Aerobic oxidations in asymmetric synthesis : catalytic strategies and recent developments // Frontiers in chemistry (2021) vol. 9, art. 614944.
https://doi.org/10.3389/fchem.2021.614944 - Kooli, A., Shalima, T., Lopušanskaja, E., Paju, A., Lopp, M. Selective C-alkylation of substituted naphthols under non-aqueous conditions // Tetrahedron (2021) vol. 95, art. 132278, 8 p. : ill.
https://doi.org/10.1016/j.tet.2021.132278 - 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 - Puthiya Veetil, S.K., Rebane, K., Yörük, C.R., Lopp, M., Trikkel, A., Hitch, M. Aqueous mineral carbonation of oil shale mine waste (limestone) : a feasibility study to develop a CO2 capture sorbent // Energy (2021) vol. 221, art. 119895.
https://doi.org/10.1016/j.energy.2021.119895 - Kaldas, K., Niidu, A., Preegel, G., Uustalu, J. M., Muldma, K., Lopp, M. Aspects of kerogen oxidative dissolution in subcritical water using oxygen from air // Oil shale (2021) 3, p. 199-214 : ill.
https://doi.org/10.3176/oil.2021.3.02 - Lopušanskaja, E., Kooli, A., Paju, A., Järving, I., Lopp, M. Towards ortho-selective electrophilic substitution/addition to phenolates in anhydrous solvents // Tetrahedron (2021) vol. 83, 12, art. 131935, 9 p.
https://doi.org/10.1016/j.tet.2021.131935 - Niidu, A., Grénman, H., Muldma, K., Kaldas, K., Mikli, V., Lopp, M. Behavior of Estonian oil shale in acidic oxidative conditions // Frontiers in Chemical Engineering (2022) vol. 4, art. 590115.
https://doi.org/10.3389/fceng.2022.590115 - Kananovich, D. G., Lopp, M. Chirogenesis in asymmetric synthesis and catalysis // Chirogenesis in Chemical Science. Singapore : World Scientific Publishing, 2023. p. 169-240.
https://doi.org/10.1142/9789811259227_0004 - Zubrytski, D. M., Elek, G. Z., Lopp, M., Kananovich, D. G. Generation of mixed anhydrides via oxidative fragmentation of tertiary cyclopropanols with phenyliodine(III) dicarboxylates // Molecules (2020) vol. 26, 1, art. 140.
https://doi.org/10.3390/molecules26010140 - Lopušanskaja, E., Paju, A., Järving, I., Lopp, M. Synthesis of cyclic 3-aryl-substituted 1,2-dicarbonyl compounds via Suzuki cross-coupling reactions // Synthesis (2018) vol. 50, 9, p. 1883-1890 : ill.
https://doi.org/10.1055/s-0036-1591543 - Maljutenko, K., Borovkov, V., Kananovich, D., Järving, I., Lopp, M. Aerobic cascade oxidation of substituted cyclopentane-1,2-diones using metalloporphyrin catalysts // Tetrahedron (2018) vol. 74, 6, p. 661−664 : ill.
https://doi.org/10.1016/j.tet.2017.12.009 - Kaldas, K., Preegel, G., Muldma, K., Lopp, M. Reactivity of aliphatic dicarboxylic acids in wet air oxidation conditions // Industrial & engineering chemistry research (2019) vol. 58, 25, p. 10855–10863 : ill.
https://doi.org/10.1021/acs.iecr.9b01643 - Kaldas, K., Preegel, G., Muldma, K., Lopp, M. Wet air oxidation of oil shales: kerogen dissolution and dicarboxylic acid formation // ACS omega (2020) vol. 5, 35, p. 22021−22030.
https://doi.org/10.1021/acsomega.0c01466 - Elek, G.Z., Koppel, K., Zubrytski, D., Konrad, N., Järving, I., Lopp, M., Kananovich, D. Divergent access to histone deacetylase inhibitory cyclopeptides via a late-stage cyclopropane ring Cleavage strategy. Short synthesis of Chlamydocin // Organic letters (2019) vol. 21, 20, p. 8473-8478 : ill.
https://doi.org/10.1021/acs.orglett.9b03305 - Aid, T., Koel, M., Lopp, M., Vaher, M. Metal-catalyzed degradation of cellulose in ionic liquid media // Inorganics (2018) vol. 6, 3, art. 78, 11 p. : ill.
https://doi.org/10.3390/inorganics6030078 - Mets, B., Kaldas, K., Uustalu, J. M., Lopp, M. The Lille-Blokker model – an excellent tool to describe the structure of kukersite // Oil shale (2023) vol. 40, 3, p. 234−243.
https://doi.org/10.3176/oil.2023.3.04 - Mets, B., Lopp, M., Uustalu, J.M., Muldma, K., Niidu, A., Kaldas, K. A two-step model for assessing the potential of shale-derived chemicals by oxidation of kukersite // Oil shale (2023) vol. 40, 4, p. 344-362.
https://doi.org/10.3176/oil.2023.4.04