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Katedra Chemii Organicznej i Medycznej (K20)

Prof. dr hab. Jacek Skarżewski

Pokój: 322 / A2
Tel: +48713202464

1972 Mgr inż. chem., (fizykochemia organiczna) Wydz. Chemiczny Politechniki Wrocławskiej
1975 Dr n. chem., (chemia organiczna), promotor: Prof. Zofia Skrowaczewska, Politechnika Wrocławska
1987 Dr hab. n. chem., (chemia organiczna), Wydz. Chem. Politechniki Wrocławskiej
2001 Prof. n. chem. (Politechnika Wrocławska)

Staże:
1976-1978 Staż po-doktorski, Gunma University, Kiryu, Japonia
1984 Universitat der Stuttgart, Niemcy

Obecne zainteresowania badwacze:
Główny obszar działalności naukowej stanowi synteza organiczna, a w szczególności wprowadzanie do syntezy nowych katalitycznych reakcji i odczynników. Prowadzone aktualnie badania, w tym także tematy prac doktorskich, dotyczą syntezy i wykorzystania chiralnych ligandów jako katalizatorów w enancjoselektywnych reakcjach z udziałem jonów metali przejściowych, a także syntezy pochodnych alkaloidów i ich zastosowania jako organokatalizatorów.

Aktualne publikacje
1. Boratyński, P.J., Kraj, A., Skarżewski, J.: "Unusual oxidative Smiles reaction of quinine 1,10-phenanthro-2-yl-thioether with SO2 extrusion." Phosphorus, Sulfur and Silicon and the Related Elements 2017, 192, 227-230.
2. Kamińska, K., Wojaczyńska, E., Skarżewski, J., Kochel, A., Wojaczyński, J.: "Application of sulfonyl chlorides and chiral amines in the efficient synthesis of nonracemic sulfinamides." Tetrahedron Asymmetry 2017, 28, 561-566.
3. Küppers, J., Schulz-Fincke, A.C., Palus, J., Giurg, M., Skarżewski, J., Gütschow, M.: "Convergent synthesis of two fluorescent ebselen-coumarin heterodimers." Pharmaceuticals 2016, 9, -.
4. Zielińska-Błajet, M., Boratyński, P.J., Sidorowicz, Ł., Skarżewski, J.: "Simple approach to modular chiral scaffolds: Binding functional sulfur nucleophiles to Cinchona alkaloids." Tetrahedron 2016, 72, 2643-2648.
5. Wojaczyńska, E., Kamińska, K., Wojaczyński, J., Skarżewski, J.: "Chiral pyrrolidine thioethers and 2-azanorbornane derivatives bearing additional nitrogen functions. Enantiopure ligands for palladium-catalyzed Tsuji-Trost reaction." Arkivoc 2016, 2017, 162-172.
6. Siedlecka, R., Wal, R., Skarżewski, J.: "One step amidine formation via reductive cyclization of (2-pyridyl)-ß-nitriles." Tetrahedron 2016, 72, 6678-6683.
7. Wojaczyńska, E., Skarżewski, J., Sidorowicz, Ł., Wieczorek, R., Wojaczyński, J.: "Zinc complexes formed by 2,2'-bipyridine and 1,10-phenanthroline moieties combined with 2-azanorbornane: Modular chiral catalysts for aldol reactions." New Journal of Chemistry 2016, 40, 9795-9805.
8. Boratyński, P.J., Nowak, A.E., Skarżewski, J.: "New Chiral Benzimidazoles Derived from 1,2-Diaminocyclohexane." Synthesis (Germany) 2015, 47, 3797-3804.
9. Wąsińska, M., Korczewska, A., Giurg, M., Skarżewski, J.: "Improved Protocol for Mononitration of Phenols with Bismuth(III) and Iron(III) Nitrates." Synthetic Communications 2015, 45, 143-150.
10. Zielińska-Błajet, M., Boratyński, P.J., Palus, J., Skarżewski, J.: "Chiral benzisoselenazolones: Conformational analysis based on experimental and DFT calculated 77Se NMR." Tetrahedron 2013, 69, 10223-10229.
11. Zielińska-Błajet, M., Skarżewski, J.: "Stereoselective dithiophosphorylation of cinchona alkaloids: Easy approach to prospective chiral ligands and organocatalysts." Phosphorus, Sulfur and Silicon and the Related Elements 2013, 188, 1811-1818.
12. Boratyński, P.J., Skarżewski, J.: "Diastereoselective Corey-Chaykovsky 9-epoxymethylation of cinchona alkaloids: Access to chiral scaffolds with diverse functionalities." Journal of Organic Chemistry 2013, 78, 4473-4482.
13. Kowalczyk, R., Nowak, A.E., Skarżewski, J.: "Organocatalytic asymmetric addition of aliphatic thiols to nitro olefins and nitrodienes." Tetrahedron Asymmetry 2013, 24, 505-514.
14. Wojaczyńska, E., Turowska-Tyrk, I., Skarżewski, J.: "Novel chiral bridged azepanes: Stereoselective ring expansion of 2-azanorbornan-3-yl methanols." Tetrahedron 2012, 68, 7848-7854.
15. Boratyński, P.J., Turowska-Tyrk, I., Skarżewski, J.: "Synthetic approaches to 9-arylated Cinchona alkaloids: Stereoselective addition of Grignard reagents to cinchonanones and hydroxylation of 9-phenylcinchonanes." Tetrahedron Asymmetry 2012, 23, 876-883.
16. Boratyński, P.J., Skarżewski, J., Sidorowicz, Ł.: "Stereochemistry of hydrophosphonylation of 9-aminoquinine Schiff bases." Arkivoc 2012, 2012, 204-215.
17. Nowak, A.E., Wojaczyńska, E., Skarżewski, J.: "Enantiopure trans-1-amino-2-(arylsulfanyl)cyclohexanes: Novel chiral motifs for ligands and organocatalysts." Tetrahedron Asymmetry 2011, 22, 1687-1691.
18. Bąkowicz, J., Skarżewski, J., Turowska-Tyrk, I.: "Photo-induced structural changes in two crystal forms with different numbers of independent molecules." CrystEngComm 2011, 13, 4332-4338.
19. Zielińska-Błajet, M., Skarżewski, J.: "Enantioselective Henry reaction catalyzed by copper(II) - Cinchona alkaloid complexes." Tetrahedron Asymmetry 2011, 22, 351-355.
20. Sidorowicz, L., Skarżewski, J.: "Easy access to 9-epimers of cinchona alkaloids: One-pot inversion by mitsunobu esterification-saponification." Synthesis 2011, 708-710.
21. Wojaczyńska, E., Zielińska-Błajet, M., Turowska-Tyrk, I., Skarżewski, J.: "Sulfoxides derived from Cinchona alkaloids - Chiral ligands in palladium-catalyzed asymmetric allylic alkylation." Tetrahedron Asymmetry 2010, 21, 853-858.
22. Boratyński, P.J., Skarżewski, J.: "New functional derivatives of 9-phenylquinine." Synthesis 2009, , 3113-3119.
23. Kowalczyk, R., Skarżewski, J.: "Asymmetric nitroaldol reaction catalyzed by copper-diamine complexes: selective construction of two contiguous stereogenic centers." Tetrahedron Asymmetry 2009, 20, 2467-2473.
24. Zielińska-Błajet, M., Skarżewski, J.: "New chiral thiols and C2-symmetrical disulfides of Cinchona alkaloids: ligands for the asymmetric Henry reaction catalyzed by CuII complexes." Tetrahedron Asymmetry 2009, 20, 1992-1998.
25. Wojaczyńska, E., Skarżewski, J.: "An effective deracemization of trans-1,2-bis (phenylsulfenyl)cyclohexane." Phosphorus, Sulfur and Silicon and the Related Elements 2009, 184, 1323-1331.
26. Kowalczyk, R., Kwiatkowski, P., Skarżewski, J., Jurczak, J.: "Enantioselective nitroaldol reaction catalyzed by sterically modified salen-chromium complexes." Journal of Organic Chemistry 2009, 74, 753-756.
27. Kowalczyk, R., Sidorowicz, Ł., Skarżewski, J.: "Asymmetric Henry reaction catalyzed by chiral secondary diamine-copper(II) complexes." Tetrahedron Asymmetry 2008, 19, 2310-2315.
28. Boratyński, P.J., Turowska-Tyrk, I., Skarżewski, J.: "Stereoselective C9 carbon-carbon couplings of quinine: Synthesis and conformational analysis of new C2-symmetric dimers." Journal of Organic Chemistry 2008, 73, 7357-7360.
29. Wojaczyńska, E., Skarżewski, J.: "Novel C2-symmetric chiral ligands: enantioselective transformation of cyclic 1,2-diols into 1,2-bis(phenylsulfenyl) and 1,2-bis(phenylselenyl) derivatives." Tetrahedron Asymmetry 2008, 19, 593-597.
30. Boratyński, P.J., Turowska-Tyrk, I., Skarżewski, J.: "Stereoselective C9 arylation and vinylation of Cinchona alkaloids." Organic Letters 2008, 10, 385-388.
31. Skarżewski, J.: "Polish Journal of Chemistry: Preface." Polish Journal of Chemistry 2007, 81, 1847-1848.
32. Kowalczyk, R., Skarżewski, J.: "Selective nucleophilic substitution using pyrazolate anions: Easy approach to modular chiral ligands with complexing pyrazole moieties." Polish Journal of Chemistry 2007, 81, 1987-1999.
33. Kowalczyk, R., Sidorowicz, Ł., Skarżewski, J.: "Asymmetric nitroaldol reaction catalyzed by a chromium(III)-salen system." Tetrahedron Asymmetry 2007, 18, 2581-2586.
34. Zielińska-Błajet, M., Siedlecka, R., Skarżewski, J.: "Chiral phenylselenyl derivatives of pyrrolidine and Cinchona alkaloids: nitrogen-selenium donating ligands in palladium-catalyzed asymmetric allylic alkylation." Tetrahedron Asymmetry 2007, 18, 131-136.
35. Drewnowski, T., Leśniak, S., Mlostoń, G., Siedlecka, R., Skarżewski, J.: "Studies on the flash vacuum thermolysis of thiones of selected N-, O-, and S-heterocycles." Helvetica Chimica Acta 2006, 89, 991-999.
36. Kowalczyk, R., Skarżewski, J.: "O-Methylatrolactic acid as a new reagent for determination of the enantiomeric purity and absolute configuration of chiral alcohols and amines." Tetrahedron Asymmetry 2006, 17, 1370-1379.
37. Zielińska-Błajet, M., Kucharska, M., Skarżewski, J.: "Simple enantiospecific synthesis of sulfides of Cinchona alkaloids." Synthesis 2006, 1176-1182.
38. Zielinska-Błajet, M., Kowalczyk, R., Skarżewski, J.: "Ring-closure reactions through intramolecular substitution of thiophenoxide by oxygen and nitrogen nucleophiles: Simple stereospecific synthesis of 4,5-dihydroisoxazoles and 4,5-dihydropyrazoles." Tetrahedron 2005, 61, 5235-5240.
39. Kowalczyk, R., Skarżewski, J.: "Regioselective synthesis of optically active (pyrazolyl)pyridines with adjacent quaternary carbon stereocenter: Chiral N,N-donating ligands." Tetrahedron 2005, 61, 623-628.
40. Siedlecka, R., Wojaczyńska, E., Skarżewski, J.: "Chiral pyrrolidine thioethers: Effective nitrogen-sulfur donating ligands in palladium-catalyzed asymmetric allylic alkylations." Tetrahedron Asymmetry 2004, 15, 1437-1444.
41. Skarżewski, J., Gupta, A., Wojaczyńska, E., Siedlecka, R.: "One-step, enantiospecific transformation of cyclic, five-membered-1, 2-diols into their respective 1,2-bis(phenylsulfanyl) derivatives." Synlett 2003, , 1615-1618.
42. Skarżewski, J., Zielińska-Błajet, M., Roszak, S., Turowska-Tyrk, I.: "Cyclization of 1,3-diaryl-3-phenylsulfanyl-1-propanols to thiochromans with the participation of [1,3]-PhS shift." Tetrahedron 2003, 59, 3621-3626.
43. Skarżewski, J., Siedlecka, R., Wojaczyńska, E., Zielińska-Blajet, M.: "A new and efficient route to homochiral ?-hydroxysulfoxides and ?-hydroxysulfones." Tetrahedron Asymmetry 2002, 13, 2105-2111.
44. Kowalczyk, R., Skarżewski, J.: "New version of the TEMPO-based catalytic system for the oxidation of alcohols to aldehydes." Polish Journal of Chemistry 2002, 76, 1413-1417.
45. Skarżewski, J., Wojaczyńska, E., Turowska-Tyrk, I.: "Sequential asymmetric dihydroxylation and sulfoxidation of homoallylic sulfides. Stereochemical aspects of the preparation of new trifunctional chiral building blocks." Tetrahedron Asymmetry 2002, 13, 369-375.
46. Skarżewski, J., Ostrycharz, E., Siedlecka, R., Zielińska-Blajet, M., Pisarski, B.: "Substituted N-salicylidene ß-aminoalcohols: Preparation and use as chiral ligands in enantioselective sulfoxidation and conjugate addition." Journal of Chemical Research - Part S 2001, , 263-264.
47. Skarżewski, J., Zielińska-Blajet, M., Turowska-Tyrk, I.: "Simple preparation of enantiomeric Michael adducts of thiophenol to chalcones: Easily available new chiral building blocks." Tetrahedron Asymmetry 2001, 12, 1923-1928.
48. Siedlecka, R., Skarzewski, J.: "Preparation and properties of 3,1-benzoxathian-4-one derivatives." Polish Journal of Chemistry 2000, 74, 1369-1374.
49. Olejnik, Z., Lis, T., Vogt, A., Wołowiec, S., Skarżewski, J.: "Single-crystal-to-single-crystal transformation of the dichloromethane solvate of the shiff base manganese(III) complex to a solvent free material." Journal of Inclusion Phenomena 2000, 38, 221-232.
50. Skarżewski, J., Ostrycharz, E., Siedlecka, R.: "Vanadium catalyzed enantioselective oxidation of sulfides: Easy transformation of bis(arylthio)alkanes into C2 symmetric chiral sulfoxides." Tetrahedron Asymmetry 1999, 10, 3457-3461.
51. Kufelnicki, A., Świaţek, M., Vogt, A., Skarżewski, J.: "The cobalt(II)-n,n'-diglycylethylenediamine-dioxygen system: A Potential Model for Metal-Peptide Interactions." Journal of Coordination Chemistry 1998, 43, 21-30.
52. Lewanowicz, A., Lipiński, J., Siedlecka, R., Skarżewski, J., Baert, F.: "Chiral ß-amino sulfoxides. Synthesis, configurational assignment and conformational analysis based on X-ray, CD, 1H NMR and theoretical calculations." Tetrahedron 1998, 54, 6571-6586.
53. Vogt, A., Wołowiec, S., Prasad, R.L., Gupta, A., Skarżewski, J.: "Synthesis and characterization of nickel(II), copper(II), manganese(III) and iron(III) complexes with new chiral salen-type ligand {N,N'-bis(3,5-di-tert-butylsalicylidene)-(1R,3S)-1,3-diamine-1,2,2- trimethylcyclopentane}." Polyhedron 1998, 17, 1231-1240.
54. Skarżewski, J., Gupta, A.: "Synthesis of C2 symmetric primary vicinal diamines. Double stereospecific Mitsunobu reaction of the heterocyclic diols derived from tartaric acid." Tetrahedron Asymmetry 1997, 8, 1861-1867.
55. Siedlecka, R., Skarżewski, J.: "Practical phase-transfer synthesis of N-(ethoxycarbonyl)phthalimide and its analogues." Synthetic Communications 1997, 27, 2081-2086.
56. Siedlecka, R., Skarżewski, J.: "Synthesis of Homochiral N-Protected ß-Amino Sulfoxides from ?-Amino Alcohols." Synlett 1996, 1996, 757-758.

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