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Asymmetric synthesis group

Logo zespołu katalizy asymetrycznej

The scientific interests of the A-Team research group focus on topics related to broadly understood organic synthesis and the use of nuclear magnetic resonance (NMR) spectroscopy in structural, mechanistic, and authentication studies. The research conducted by the group provides innovative solutions and synthetic methods, contributing to the advancement of modern organic chemistry. The leader of the team is Prof. Łukasz Albrecht.

The main research areas include:

  • Stereocontrolled synthesis of biologically important compounds
  • Design of new organocatalysts and novel methods for catalytic activation of molecules
  • Development of new photo- and electrochemical reactions
  • Investigation of the mechanisms of organocatalytic reactions using kinetic and synthetic techniques, with a particular emphasis on the application of nuclear magnetic resonance (NMR) spectroscopy
  • Use of NMR spectroscopy in medical diagnostics
  • Authentication of products using NMR spectroscopy methods

     

    Treść (rozbudowana)
    Selected papers
    1. Identifying the Botanical Origin of Alcohol Using 2H SNIF NMR: A Case Study of “Polish Vodka” PGI Ciepielowski, G, Krassowski, J., Albrecht, L., Pacholczyk-Sienicka, B. Food Chemistry 2025, 463, 141218.
    2. Asymmetric [4+2]-Cycloaddition of Anthracene Derivatives via Hydrazone Activation Łukasik, B., Ossowski, J., Frankowski, S., Albrecht, Ł. Adv. Synth. Catal. 2024, 366, 704 Polyenolate-mediated reaction cascade initiated by higher-order-cycloaddition for the construction of polycarbocyclic scaffolds
    3. Cieśliński, A., Skrzyńska, A., Przydacz, A., Albrecht, Ł. Org. Chem. Front. 2024, 11, 1700. Hydrazone Activation in the Aminocatalytic Cascade Reaction for the Synthesis of Tetrahydroindolizines
    4. Kowalska, J., Łukasik, B., Frankowski, S., Albrecht, Ł. Org. Lett. 2024, 26, 814.
    5. Crimes against food: characteristics, health risk and regulations Pacholczyk-Sienicka, B. Food and Energy Security 2024, 13:e700002.
    6. Comparative analysis of bioactive compounds in garlic owing to the cultivar and origin Pacholczyk-Sienicka, B., Modranka, J., Ciepielowski, G. Food Chemistry, 2024, 439, 138141.
    7. Dearomative, aminocatalytic formal normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines Dyguda, M., Przydacz, A., Albrecht, Ł. Chem. Commun. 2023, 59, 12903.
    8. Synthesis of cyclopent-1-enecarbonitriles via a tandem Giese/HWE reaction initiated by visible light Moczulski, M., Deredas, D., Kuśmierek, E., Albrecht, Ł., Albrecht, A. Chem. Commun. 2023, 59, 4372
    9. Vinylogous Hydrazone Strategy in Stereoselective Synthesis of 2,3-Dihydro-1H-pyrrolizines – An Organocatalytic, Metal-Free Route to Ketorolac Kowalska, J.; Łukasik, B.; Frankowski, S.; Sieroń, L.; Albrecht, Ł. Adv. Synth. Catal. 2022, 364, 3607–3616.
    10. Classification of Polish Natural Bee Honeys Based on Their Chemical Composition Pacholczyk-Sienicka, B.; Ciepielowski, G.; Modranka, J.; Bartosik, T.; Albrecht, Ł. Molecules 2022, 27, 4844.
    11. NHC-Catalyzed 1,4-Elimination in the Dearomative Activation of 3-Furaldehydes towards (4+2)-Cycloadditions Przydacz, A.; Topolska, A.; Skrzyńska, A.; Albrecht, Ł. Adv. Synth. Catal. 2022, 364, 1434–1439.
    12. Dearomative Michael addition involving enals and 2-nitrobenzofurans realized under NHC-catalysis Dyguda, M.; Skrzyńska, A.; Sieroń, L.; Albrecht, Ł. Chem. Commun. 2022, 58, 5367–5370.
    13. Differentiating Catalysis in the Dearomative [4 + 2]-Cycloaddition Involving Enals and Heteroaromatic Aldehydes Topolska, A.; Frankowski, S.; Albrecht, Ł. Org. Lett. 2022, 24, 955–959.
    14. Vinylogous hydrazone strategy for the organocatalytic alkylation of heteroaromatic derivatives Łukasik, B.; Kowalska, J.; Frankowski, S.; Albrecht, Ł. Chem. Commun. 2021, 57, 6312-6315.
    15. 2-Selenouridine, a Modified Nucleoside of Bacterial tRNAs, Its Reactivity in the Presence of Oxidizing and Reducing Reagents. Kulik, K., Sadowska, K., Wielgus, E., Pacholczyk-Sienicka, B. Sochacka, E., Nawrot, B. Int. J. Mol. Sci. 2022, 23, 7973.
    16. UHPLC-DAD-ESI-HRMS/MS profile of phenolic compounds in northern red oak (Quercus rubra L., syn. Q. borealis F. Michx) seeds and its transformation during thermal processing Oracz, J., Żyżelewicz, D., Pacholczyk-Sienicka, B. Industrial Crops and Products, 2022, 189, 115860.
    17. Enantioselective H-bond-directed vinylogous iminium ion strategy for the functionalization of vinyl-substituted heteroaryl aldehydes Skrzyńska, A.; Frankowski, S.; Topolska, A.; Dyguda, M.; Gao, X.-Y.; Xu, C.-J.; Chen, Y.-C.; Albrecht, Ł. Chem. Commun. 2021, 57, 1667-1670.
    18. Enantioselective H-bond-directed vinylogous iminium ion strategy for the functionalization of vinyl-substituted heteroaryl aldehydes Skrzyńska, A.; Frankowski, S.; Topolska, A.; Dyguda, M.; Gao, X.-Y.; Xu, C.-J.; Chen, Y.-C.; Albrecht, Ł. Chem. Commun. 2021, 57, 1667–1670.
    19. 1,3,4-Thiadiazoles effectively inhibit proliferation of toxoplasma gondii Węglińska, L.; Bekier, A.; Dzitko, K.; Pacholczyk-Sienicka, B.; Albrecht, Ł.; Plech, T.; Paneth, P., Paneth, A. Cells 2021, 10, 1053.
    20. The application of NMR spectroscopy and chemometrics in authentication of spices Pacholczyk-Sienicka, B.; Ciepielowski, G.; Albrecht, Ł. Molecules 2021, 26, 382.
    21. The first application of 1H NMR spectroscopy for the assessment of the authenticity of perfumes Pacholczyk-Sienicka, B.; Ciepielowski, G.; Albrecht, Ł. Molecules 2021, 26, 3098.
    22. Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels-Alder Reaction Saktura, M.; Grzelak, P.; Dybowska, J.; Albrecht, Ł. Org. Lett. 2020, 22, 1813-1817.
    23. The Game of Electrons: Organocatalytic Higher‐Order Cycloadditions Involving Fulvene‐ and Tropone‐Derived Systems Frankowski, S.; Romaniszyn, M.; Skrzyńska, A.; Albrecht, Ł. Chem. Eur. J. 2020, 26, 2120-2132.
    24. The influence of experimental parameters on quantitative deuterium measurements for ethyl alcohols of different origin Ciepielowski, G.; Pacholczyk-Sienicka, B.; Klajman, G.; Paneth, P.; Albrecht, Ł. J. Sci. Food Agric. 2020, 100, 1812-1815.
    25. Asymmetric Formal Vinylogous Iminium Ion Activation for Vinyl-Substituted Heteroaryl and Aryl Aldehydes Gao, X.-Y.; Yan, R.-J.; Xiao, B.-X.; Du, W.; Albrecht, Ł.; Chen, Y.-C. Org. Lett. 2019, 21, 9628-9632.
    26. Inverting the reactivity of troponoid systems in enantioselective higher-order cycloaddition Frankowski, S.; Skrzyńska, A.; Albrecht, Ł. Chem. Commun. 2019, 55, 11675-11678 (cover paper).
    27. Breaking Aromaticity with Aminocatalysis: A Convenient Strategy for Asymmetric Synthesis  Przydacz, A.; Skrzyńska, A.; Albrecht, Ł. Angew. Chem. Int. Ed. 2019, 58, 63–73.
    28. Site-Selective and Enantioselective α,β,γ-Functionalization of 5-Alkylidenefuran-2(5H)-ones: A Route to Polycyclic γ-Lactones Skrzyńska, A.; Frankowski, S.; Moczulski, M. Drelich, P.; Albrecht, Ł. Org. Lett. 2019, 21, 1248–1252.
    29. Comparison of quantitative NMR and IRMS spectrometry for the authentication of Polish Vodka Ciepielowski, G.; Pacholczyk-Sienicka, B.; Frączek, T.; Klajman, G.; Paneth, P.; Albrecht, Ł. J. Sci. Food Agric. 2019, 99, 263–268.
    30. Synthesis of γ,γ-Disubstituted Butenolides through a Doubly Vinylogous Organocatalytic Cycloaddition Skrzyńska, A.; Drelich, P.; Frankowski, S.; Albrecht, Ł. Chem. Eur. J. 2018, 24, 16543 (Highlighted in Synfacts).
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