Investigations on the Iron-Catalyzed Asymmetric Sulfide Oxidation

✍ Scribed by Julien Legros; Carsten Bolm

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 167 KB
• Volume: 11
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200400857

✦ Synopsis

Abstract

The development of an enantioselective sulfide oxidation involving a chiral iron catalyst and aqueous hydrogen peroxide as oxidant is described. In the presence of a simple carboxylic acid, or a carboxylate salt, the reaction affords sulfoxides with remarkable enantioselectivities (up to 96 % ee) in moderate to good yields. The influence of the structure of the additive on the reaction outcome is reported. In the sulfoxide‐to‐sulfone oxidation a kinetic resolution (with s=4.8) occurs, which, however, plays only a negligible role in the overall enantioselective process. Furthermore, a positive nonlinear relationship between the ee of the product and that of the catalyst has been found. On the basis of these observations, a possible catalyst structure is proposed.