ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

New substituted mono-and bis(imidazolyl)pyridines and their application in nitroaldolisation reaction

R. Keder, P. Drabina, J. Hanusek, and M. Sedlák

Department of Organic Chemistry, Faculty of Chemical Technology, University of Pardubice, CZ-532 10 Pardubice, Czech Republic

E-mail: milos.sedlak@upce.cz

Received: 24 March 2006  Revised: 5 May 2006  Accepted: 2 June 2006

Abstract: New chiral nitrogen ligands based on the substituted mono-and bis(imidazolyl)pyridines have been prepared and characterised. Their complexes with cupric acetate were used as catalysts in the nitroaldolisation reaction. In the case of optically pure complexes of mono(imidazolyl)pyridine, the isolated products were 2-nitro-1-(2-nitrophenyl)ethanols or 2-nitro-1-(4-nitrophenyl)ethanols in overall yields of 49–93 % and with the maximum enantiomeric excess of 15.6 %. The complexes of bis(imidazolyl)pyridine also catalyse the nitroaldol reaction, the yields being 64–90 %, but with zero enantioselective excess.

Keywords: imidazolylpyridines - catalysis - copper complex - aldolisation reaction

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-006-0059-z

Chemical Papers 60 (4) 324–326 (2006)