Laboratory of Stereocontrolled Organic Synthesis

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LABORATORY OF STEREOCONTROLLED ORGANIC SYNTHESIS

Head of the laboratory:

prof. Rafał Siciński

Academic Staff:

  • prof. Tomasz Bauer
  • Anna Piątek, DSc
  • Piotr Piątek, DSc
  • Michał Chmielewski, PhD
  • Piotr Kwiatkowski, PhD
  • Jan Romański, PhD
  • Katarzyna Sęktas, PhD
  • Krzysztof Ziach, PhD

PhD Students:

  • Krzysztof Bąk
  • Paweł Brzemiński
  • Martyna Cybularczyk
  • Adrian Fabisiak
  • Anna Nowak
  • Monika Nowakowska
  • Adam Rajkiewicz
  • Jan Rzymkowski
  • Marcin Szybiński
  • Magdalena Walewska-Królikiewicz
  • Maciej Zakrzewski
  • Dominika Załubiniak
  • Anna Zep

Website address:

http://psso.chem.uw.edu.pl/

Areas of scientific activity:

  1. Synthesis of steroid hormones agonists and antagonists
  2. Design, synthesis and evaluation of cytotoxic properties of structurally modified vitamin D compounds
  3. Design, synthesis and investigation of binding properties of molecular anions, salts and neutral molecules receptors, anion transport through biological membranes, fotoswitchable receptors for anions
  4. Metal-Organic Frameworks (MOFs), crystalline coordination polymers having in their crystal structures empty voids of nanoscopic dimensions (cavities, channels, etc.); application in heterogeneous catalysis
  5. Anion templated synthesis of catenanes and rotaxanes
  6. Synthesis and application of new chiral Lewis acids
  7. High-pressure activation of enantioselective organocatalytic reactions
  8. Asymmetric synthesis of fluoroorganic compounds
  9. Development of enantioselective methods for the construction of quaternary stereogenic center
  10. Asymmetric hydrogenation and tetrasubstituted alkenes synthesis as tools in preparation of biologically active compounds
  11. Achmatowicz rearrangement of optically active α,β-unsaturated alcohols and amines as a tool in the synthesis of biologically active compounds
  12. Synthesis of steroid transition metal complexes as potential anticancer drugs
  13. Dynamic combinatorial chemistry of imines
  14. Supramolecular systems of “molecular walkers”
  15. Photochemistry of polyenes
  16. Spontaneous emergence of solid state chirality in achiral systems

Major scientific achievements:

The information available on the individual websites of Academic Staff

Selected topics of Bachelor and Master theses:

Supervisor: Anna Piątek, DSc
The asymmetric hydrogenation of tetrasubstituted alkenes.

Supervisor: Jan Romański, PhD
Modification of polymeric systems with molecular receptors.
Synthesis and binding abilities of ion pair receptors based on 3-aminobenzoic acid.

Supervisor: prof. Tomasz Bauer
Synthesis and enantioselective alkenylation of N-sulfonyl furylimines.
Total synthesis of (S)-4-(tert-butoxycarbonylamino)-2-phenylbutanoic acid.
Total synthesis of (S)-4-amino-3-phenylbutanoic acid.
Total synthesis of (R)-3-(tert-butoxycarbonylamino)-2-phenylbutanoic acid.
Optically active Betti’s base: its synthesis and application for the alkenylation of furfural.

Supervisor: prof. Rafał Siciński

Preparation and functionalization of lactone of the natural (1R,3R,4S,5R)-(-)-quinic acid.
Total synthesis of chiral bicycloheptanones.
Synthesis of (3R,4S,5R)-(-)-shikimic acid derivates.
Enantioselective synthesis of the vitamin D side chains.
Epoxidation of (S)-carvone and its functionalization.

Supervisor: Katarzyna Sęktas, PhD
Synthesis of  thiol cholecalciferol derivates as ligands in the gold complexes.
Application of Suzuki reaction to the synthesis of steroid ligands.

Supervisor: Piotr Kwiatkowski, PhD
Enantioselective synthesis of trifluoromethylated compounds.
High-pressure activation of selected catalytic organic reactions.
Development of novel asymmetric organocatalytic reactions.
Catalytic enantioselective conjugate additions to β,β-disubstituted Michael acceptors.

Supervisor: Krzysztof Ziach, PhD
Hydrophobic receptors of the neutral molecules.
Synthesis of  building blocks of  a molecule of a „molecular walker.”

Supervisor: Michał Chmielewski, PhD
Supramolecular Chemistry Laboratory (located in the new building of Biological and Chemical Research Centre)
Innovative materials for catalysis: synthesis and catalytic properties of novel metal organic frameworks (MOFs).
Supramolecular chemistry of anions: fluorescent sensors and transporters of anions based on 1,8-diaminocarbazole skeleton – synthesis and anion binding properties.
Supramolecular chemistry of anions: synthesis and binding properties of anion selective fluorescent rotaxanes and catenanes.
Supramolecular chemistry: photoswitchable receptors based on acylhydrazone groups – synthesis and binding properties.

Supervisor: Piotr Piątek, DSc
Development of the synthetic method for the preparation of hydroxymethyl 18-crown-6.
The study of ionophoric activity of selected salt receptors.
The synthesis of N-alkyl derivatives of 1H-pyrazole-1-carboxamidine and their application as guanylating agents.

Major research projects and international cooperation:

The information available on the individual websites of Academic Staff