Division of Heteroorganic Chemistry

The research conducted in the Department focuses on the following subjects:

  • Chemistry, stereochemistry and bioorganic chemistry of organic phosphorus, sulfur and to a lesser extent selenium and tellurium compounds and their use as catalysts.
  • Application of heteroorganic compounds in asymmetric synthesis and in the total      synthesis of natural and biologically active compounds.
  • Biocatalysis in heteroorganic chemistry.
  • Chemistry of new materials.

The Department comprises of five research groups. Two of them are formally separated: “Laboratory of Stereochemistry”, headed by Professor Józef Drabowicz and “Laboratory of Metallo- and Metalloidoorganic Chemistry”, headed by Professor Piotr Bałczewski. The remaining informal three groups are headed by: Professor Marian Mikołajczyk, Associate Professor  Wanda  H. Midura (DSc.) and Professor Piotr Kiełbasiński. All the groups closely cooperate within the Department and contribute to all the research subjects mentioned above.

The research interest in stereochemistry is related to new asymmetric and stereoselective syntheses of organic phosphorus and sulfur compounds in which these heteroatoms are stereogenic centres. In addition to classical chemical syntheses of these compounds, application of biocatalysts (enzymes or crude cell preparations) is a very important and fast developing area of research allowing for the synthesis of chiral non-racemic heteroorganic derivatives that are otherwise inaccessible. The optically active heteroorganic substrates are applied in the synthesis of new chiral catalysts and ligands for organometallic chemistry and in the asymmetric synthesis of various biologically active compounds, such as chiral aminophosphonic acids and cyclopropanes of biological importance. Phosphorus, sulfur and selenium – containing reagents are used as valuable substrates in the synthesis of biologically active natural products. In this way, syntheses of a series of cyclopentanoid antibiotics and various drugs, such as methylenomycines, sarkomycin, rosaprostol, neplanocin, prostaglandins and their derivatives, have been accomplished. Another field is the synthesis of heteroorganic dendrimers used as drugs and drug carriers.

Chemistry of new materials comprises investigations on the synthesis of polythiophene  derivatives and, applying a methodology originally developed in the Department, synthesis of polycyclic aromatic and heteroaromatic hydrocarbons as potential substrates for organic molecular electronics devices, biologically active compounds and organometallic catalysts.

  1. J. Drabowicz, D. Krasowska, J. Chrzanowski, A.Zając, “Chirality of Hypervalent Chalcogenuranes”, Curr. Org. Chem, 2016, 20, 146-154.
  2. M. Koprowski, P. Bałczewski, K. Owsianik, E. Różycka-Sokołowska,, “Total synthesis of (±)-epithuriferic acid methyl ester via Diels-Alder reaction”, Org. Biomol. Chem. 2016, 14, 1822 – 1830.
  3. B. Łukasik, W. Perlikowska, R. Żurawiński, M. Mikołajczyk,, “Synthesis of Enantiomerically Pure Stereomers of Rosaprostol”, J. Org. Chem. 2015, 80, 9798–9802.
  4. W. H. Midura, J. Krysiak,, „Highly asymmetric cyclopropanation with  two sulfinyl auxiliaries”, Chirality 2015, 27, 816–819.
  5. M. Rachwalski, Z. Wujkowska, S. Leśniak, P. Kiełbasiński, “Highly efficient asymmetric aziridination of unsaturated aldehydes promoted by chiral heteroorganic catalysts”, ChemCatChem 2015, 7, 3589-3592.
  6. J. Pecyna, A. Jankowiak, D. Pociecha, P. Kaszyński, “o-Carborane derivatives for probing molecular polarity effects on liquid crystal phase stability and dielectric behavior”, J. Mater. Chem. C. 2015, 3, 11412—11422.
  7. B. Łukasik, M. Mikołajczyk, G. Bujacz, R. Żurawiński, „Synthesis and absolute configuration of both enantiomers of 4,5-dihydro-3-(formyl)cyclopent-2-enone acetonide as a new chiral building block for prostanoid synthesis”, Org. Biomol. Chem.  2015, 13 , 807-816.
  8. S. M. Mignani, M. Bryszewska, B. Klajnert-Maculewicz, M. Zabłocka, J.-P. Majoral,, “Advances combination therapies based on nanoparticles for efficacious cancer treatment: an analytic report”, Biomacromolecules  2015, 16, 1-27.
  9. P. Bałczewski, J. Skalik, P. Uznański, D. Guziejewski, W. Ciesielski,, “Use of isomeric, aromatic dialdehydes in synthesis of photoactive, positional isomers of higher analogs of  o-bromo(hetero)acenaldehydes”, RSC Adv. 2015, 5, 24700–24704.
  10. D. Krasowska, J. Chrzanowski, J. Drabowicz, “Heterocycles with a stereogenic phosphorus or sulfur atom derived from aminoalcohols or aminonaphthols”, Adv. Heterocycl. Chem. 2015, 117, 179-259.
  11. G. Salamończyk, “Efficient synthesis of water-soluble, phosphonate-terminated polyester dendrimers”, Tetrahedron Lett. 2015, 56, 7161-7164.
  12. E. Krawczyk, M. Koprowski, G. Mielniczak, K. Owsianik, “Asymmetric Synthesis of 5,7-O-Dimethyleucomols via Enantioselective  Oxidation of Enol Phosphates”, Tetrahedron: Asymmetry 2015, 26, 876–883.
  13. B. Bujnicki, J. Drabowicz, M. Mikołajczyk, „Acid catalyzed alcoholysis of sulfinamides: unusual stereochemistry, kinetics and a question of mechanism involving sulfurane intermediates and their pseudorotation”, Molecules 2015, 20, 2949-2972.
  14. R. Biczak, B. Pawłowska, P. Bałczewski, P. Rychter,, “The role of the anion in the toxicity of imidazolium ionic liquids”, J. Hazard. Mat.  2014, 274, 181-190.
  15. P. Kiełbasiński, J. Łuczak, T. Cierpiał, J. Błaszczyk, L. Sieroń, K. Wiktorska, K. Lubelska, M. Milczarek, Z. Chilmończyk,, “New enantiomeric fluorine-containing derivatives of sulforaphane: synthesis, absolute configurations and biological activity”, Eur. J. Med. Chem. 2014, 76, 332-342.
  16. M. Mikina, M. Mikołajczyk, „The sila-Pummerer reaction of γ-silyl substituted cycloalkanonyl sulfoxides: the first examples and a new approach to 3-substituted cycloalk-2-enones”, Tetrahedron Lett.  2014, 55, 3954-3956.
  17. M. Rachwalski, S. Kaczmarczyk, S. Leśniak, P. Kiełbasiński,, “Highly efficient asymmetric Simmons-Smith cyclopropanation promoted by chiral heteroorganic aziridinyl ligands”, ChemCatChem 2014, 6, 873-875.
  18. P. Kiełbasiński, M. Rachwalski, S. Kaczmarczyk, S. Leśniak, “Polydentate chiral heteroorganic ligands/catalysts – impact of particular  functional groups on their activity in selected reactions of asymmetric synthesis”, Tetrahedron: Asymmetry 2013, 24, 1417-1420.
  19.  W. H. Midura, J. Krysiak, A. Rzewnicka, A. Supeł, P. Łyżwa, A. M. Ewas, “Asymmetric synthesis of conformationally constrained L-AP4 analogues using chiral sulfinyl auxiliary”, Tetrahedron 2013, 69, 730-737.
  20. P. Łyżwa, J. Błaszczyk, L. Sieroń, M. Mikołajczyk    “Asymmetric synthesis of structurally diverse aminophosphonic acids using enantiopure N-p-toluenesulfinyl cinnamaldimines as reagents”, Eur. J. Org. Chem. 2013, 2106-2115.
  21. L. Madalińska, M. Kwiatkowska, T. Cierpiał, P. Kiełbasiński:, “Investigations of enzyme catalytic promiscuity: the first attempts at a hydrolytic enzyme-promoted conjugate additions of nucleophiles to α,β-unsaturated sulfinyl acceptors”, J. Mol. Catal. B: Enzym. 201281, 25-30.
  22. A. Bodzioch, B. Marciniak, E. Różycka-Sokołowska, J. K. Jeszka, P. Uznański, S. Kania, J. Kuliński, P. Bałczewski:, “Synthesis and Optoelectronic Properties of Hexahydroxylated 10-OSubstituted Anthracenes via a New Modification of the Friedel-Crafts Reaction Using O-Protected ortho-Acetal Diarylmethanols”, Chem. – Eur. J. 201218, 4866-4876.
  23. M. Mikołajczyk, J. Łuczak, L. Sieroń, M. W. Wieczorek: “Stereoselective synthesis of enantiomeric tetramethylammonium 2-oxo-thio-1,3,2-oxazaphosphorinanes as key precursors to structurally diverse chiral derivatives”. Tetrahedron  2012, 68, 126-132.
  24. S. Kaczmarczyk, M. Kwiatkowska, L. Madalińska, A. Barbachowska, M. Rachwalski, J. Błaszczyk, L. Sieroń, P. Kiełbasiński:, “Enzymatic synthesis of enantiopure precursors of chiral bidentate and tridentate phosphorus catalysts”., Adv. Synth. Catal. 2011353, 2446-2454.
  25. M. Kwiatkowska, G. Krasiński, M. Cypryk, T. Cierpiał, P. Kiełbasiński:, “Lipase-mediated stereoselective transformations of chiral organophosphorus P-boranes revisited: revision of the absolute configuration of alkoxy(hydroxymethyl)phenyl-phosphine P-boranes”. , Tetrahedron: Asymmetry 201122, 1581-1590.
  26. W. Perlikowska, M. Mikołajczyk:, “A new and concise approach to enantiomers of phytoprostane B1 type II”. , Tetrahedron: Asymmetry, 201122, 1767-1771.
  27. E. Krawczyk, K. Owsianik:, „An unusual regiochemistry of reactions of cyclohexenylphosphonate bearing β-ethoxycarbonyl group with aldehydes”.   , Tetrahedron 201167, 1938-1947.
  28. G. Salamończyk:, “Synthesis of dendrimers, trimesic acid derivatives”. , Tetrahedron Lett. 201152, 155-158.
  29. P. Bałczewski A. Bodzioch, E. Różycka-Sokołowska, B. Marciniak, P. Uznański:, „A new one-pot transformation of the O-protected diarylmethanols to nitrogen containing fused aromatic hydrocarbons as potential materials for organic electronic devices (OFETs and OLEDs)”.  , Chem.- Eur. J201016, 2392-2400.
  30. M. Zabłocka, A. Hameau, A.-M. Caminade, J.-P. Majoral:, „Cage-like” phosphines. Design, and catalytic properties.”, Adv. Synth. Catal. 2010352, 2341-2358.
  31. P. Łyżwa, M. Mikołajczyk:, „Asymmetric synthesis of aminophosphonic acids mediated by chiral sulfinyl auxiliaries”. , Pure Appl. Chem. 201082, 577-582.
  32. R. Żurawiński, M. Mikina, M. Mikołajczyk:, “Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues (-) and (+)-TEI 9826”. , Tetrahedron: Asymmetry 201021, 2794-2799.
  33. J. Krysiak, W. H. Midura, W. Wieczorek, L. Sieroń, M. Mikołajczyk:, „Constrained cycloalkyl analogues of glutamic acid: stereocontrolled synthesis of (+)-2- aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740) and its 6-phosphonic  analogue”. , Tetrahedron: Asymmetry 2010, 21, 1486-1493.
  34. J. Drabowicz, D. Krasowska, A. Łopusiński, C. V. Stevens, T. S. A. Heugeberth:, „Cyclic tri and pentavalent amidoesters and diamides with a stereogenic phosphorus atom   in asymmetric synthesis. Part I: Stoichiometric reagents”. , Current  Organic Chemistry 201014, 483-499.
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