title: Copper-catalyzed asymmetric oxidation of sulfides.
abstract: Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence of variation of solvent and ligand structure was examined, and the optimized conditions were then used to oxidize a number of aryl alkyl and aryl benzyl sulfides, producing sulfoxides in excellent yields in most cases (up to 92%), and good enantiopurities in certain cases (up to 84% ee).
authors.affiliation: Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland.
authors.forename: Graham E
authors.initials: GE
authors.lastname: O'Mahony
authors.forename: Alan
authors.initials: A
authors.lastname: Ford
authors.forename: Anita R
authors.initials: AR
authors.lastname: Maguire
mesh_terms: D000473:Alkanes / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000473:Alkanes; D008024:Ligands; D013440:Sulfides; D013454:Sulfoxides; D003300:Copper; D006861:Hydrogen Peroxide