【精选】2006-TA-Studies on enzymatic synthesis of chiral non-racemic 3-arylglutaric acid monoesters.pdf

Tetrahedron: Asymmetry 17 (2006) 961–966 Studies on enzymatic synthesis of chiral non-racemic 3-arylglutaric acid monoesters Anna Fryszkowska,a Marta Komar,b Dominik Koszelewskib and Ryszard Ostaszewskia,b,* aFaculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland bInstitute of Organic Chemistry PAS, Kasprzaka 44/52, 01-224 Warsaw, Poland Received 31 January 2006; accepted 7 March 2006 Available online 4 April 2006 Abstract—The enantioselective enzymatic desymmetrization (EED) of various 3-arylglutaric anhydrides 1 with alcohols in organic media has been studied. The effect of the solvent on the stereochemical outcome of the reaction was investigated in detail. The amount of bio- catalyst was optimized, and the possibility of its re-use was tested. The first example of the EED of 3-substituted glutaric anhydrides with esters as nucleophiles is reported. 2006 Elsevier Ltd. All rights reserved. 1. Introduction Cl Desymmetrization of meso and prochiral compounds is a powerful approach in asymmetric synthesis.1,2 In contrast NH O O to a kinetic resolution, a maximum yield of 100% can be HOOC NH . HCl H N achieved in a single-step reaction based on enantiofacial 2 2 N OH