Combination of enzymatic procedures with multicomponent condensations

Ostaszewski, R.; Portlock, D. E.; Fryszkowska, Anna; Jeziorska, Katarzyna

doi:10.1351/pac200375020413

Pure Appl. Chem., 2003, Vol. 75, No. 2-3, pp. 413-419

http://dx.doi.org/10.1351/pac200375020413

Combination of enzymatic procedures with multicomponent condensations

R. Ostaszewski^1,2*, D. E. Portlock³, Anna Fryszkowska¹ and Katarzyna Jeziorska¹

¹ Faculty of Chemistry, Warsaw University of Technology, 00-664 Warsaw, Noakowskiego 3, Poland
² Institute of Organic Chemistry PAS, 01-224 Warsaw, Kasprzaka 44/52, Poland
³ Combinatorial Chemistry Section, Procter & Gamble Pharmaceuticals, Health Care Research Center, 8700 Mason Montgomery Road, Mason, OH 45040, USA

Abstract: A new synthetic method based on combination of enzymatic desymmetrization of 3-phenylglutaric anhydrides with multicomponent condensation is outlined. Enzymatic monoesterification of glutaric anhydrides was performed, and the derived monoacids were used as substrates for subsequent Ugi and Passerini multicomponent condensations. Both reactions were combined as two-step, one-pot processes. The choice of solvent and enzyme type has an appreciable effect on the course of reactions.