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Group VI
ASYMMETRIC CATALYSIS: APPLICATION OF CHIRAL LEWIS AND BRØNSTED ACIDS

Head of  the group:

Assoc. Prof. Jacek Młynarski

e-mail: <mlynar@icho.edu.pl> 

Ph.D., Institute of Organic Chemistry Polish Academy of Sciences, Warsaw, Poland, 2000

Foundation for Polish Science Fellowship, 2000

Prime Minister of Polish Government Prize, 2001

Post-doc, MPI, Mülheim a.d. Ruhr, Germany, 2001-2002 (Prof. Alois Fürstner)

Alexander von Humboldt Fellowship, 2001

Habilitation, Institute of Organic Chemistry Polish Academy of Sciences, Warsaw, Poland, 2006

Polish Academy of Sciences Włodzimierz Kołos Prize, 2007

 Homepage of the group: http://jacekmlynarski.pl

Staff:

Maciej Stodulski Ph.D. Student, Joanna Paradowska Ph.D. Student, Agnieszka Mamińska M.Sc. Student, Maria Rogozińska M.Sc. Student

Research activity

Research in our group is focused on organic synthesis and the discovery of new reaction methodology, in particular stereoselective and catalytic asymmetric reactions. Our current research interest involves enantioselective synthetic methodology rely on metal-based chiral catalysts. The following topics are recently being studied in our laboratories:

1. Tandem asymmetric aldol reaction/reduction leading stereoselectively to anti-1,3-diols.

2. Development of water-compatible chiral Lewis acids.

3. Designing of new catalysts for direct asymmetric aldol and aldol-type reactions in water.

4. Synthesis of novel pybox-type ligands for asymmetric aqua-Mukaiyama reaction (designing of water-compatible chiral Zn and Fe complexes).

5. Towards enzyme mimics: direct aldol reaction in water promoted by chiral Zn(II) complexes as well as small organic molecules.

Selected scientific publications: 

1.    Paradowska, J.; Stodulski, M.; Mlynarski, J.: Direct Catalytic Asymmetric Aldol Reactions Assisted by Zinc Complex in the Presence of Water
Adv. Synth. Catal
.
2007, 239, 1041-1046

2.     Jankowska J.; Paradowska, J.; Rakiel, B.; Mlynarski, J.: Iron(II) and Zinc(II) Complexes with Designed pybox Ligands for the Asymmetric Aqueous Mukaiyama-Aldol Reactions    
J. Org.
Chem. 2007, 72, 2228-2231

3.    Mlynarski, J.: Direct Asymmetric Aldol-Tishchenko Reaction Microreview
Eur. J. Org. Chem. 2006, 4779-4786

4.    Mlynarski, J., Rakiel B.; Stodulski, M.; Suszczyńska, A., Frelek, J.: The Chiral Ytterbium Complexes-Catalyzed Direct Asymmetric Aldol-Tishchenko Reaction. Synthesis of anti-1,3-Diols            
Chem. Eur. J. 2006, 12, 8158-8167

5.    Jankowska J.; Paradowska, J.; Mlynarski, J.: A Chiral Iron(II)–Pybox Catalyst Stable in Aqueous Media. Asymmetric Mukaiyama–Aldol Reaction     
Tetrahedron Lett. 2006, 47, 5281-5284

6.    Jankowska, J.; Mlynarski, J.: Zn(pybox)-Complex Catalyzed Asymmetric Aqueous Mukaiyama-Aldol Reactions
J. Org. Chem. 2006, 71, 1317-1321

7.    Mlynarski, J.; Jankowska J.; Rakiel, B.: Direct Asymmetric Aldol-Tishchenko Reaction of Aliphatic Ketones Catalyzed by syn-Aminoalcohol-Yb(III)-Complexes  
Chem. Commun. 2005, 4854-4856

8.    Mlynarski, J.; Jankowska, J.; Rakiel, B.: Synthesis of Chiral Hybrid O,N-Donor Ligands for the Investigation of Lanthanide Complex Reactivity in Direct Aldol Condensation    
Tetrahedron: Asymmetry
2005, 8, 1521-1526

9.    Mlynarski, J.; Jankowska, J.: Asymmetric Mukaiyama-Aldol Reaction in Aqueous Media Promoted by Zinc-Based Chiral Lewis Acids            
Adv. Synth. Catal. 2005, 347, 521-525

10.  Mlynarski, J.; Mitura, M.: The First Example of Aldol-Tishchenko Reaction of Aldehydes and Aliphatic Ketones
Tetrahedron Lett. 2004, 45, 7549-7552