Asymmetric Synthesis of Aryl Benzyl Sulfoxides by Vanadium-Catalysed Oxidation: A Combination of Enantioselective Sulfide Oxidation and Kinetic Resolution in Sulfoxide Oxidation

✍ Scribed by Pádraig Kelly; Simon E. Lawrence; Anita R. Maguire

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 171 KB
• Volume: 2006
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200600320

✦ Synopsis

Abstract

Enantioselective vanadium‐catalysed oxidation of aryl benzyl sulfides using Bolm’s procedure is accompanied by kinetic resolution in the oxidation of the resulting sulfoxides which enhances the enantiopurities of the sulfoxides recovered (typically >90 % ee), albeit with an associated reduction in yield. The effects of ligand, solvent and reaction conditions are discussed in detail.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)