ChemInform Abstract: Enantioselective Catalytic Oxidation of (Arylthio)- or (Alkylthio)methylphosphonates as a Route to Enantiomeric Pure Aryl Alkyl or Dialkyl Sulfoxides.

✍ Scribed by Maria Annunziata M. Capozzi; Cosimo Cardellicchio; Giuseppe Fracchiolla; Francesco Naso; Paolo Tortorella

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 31 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199935107

✦ Synopsis

1999

sulfoxides, sulfones, sulfenes and derivatives sulfoxides, sulfones, sulfenes and derivatives (benzene compounds) Q 0600

35 -107

Enantioselective Catalytic Oxidation of (Arylthio)-or (Alkylthio)methylphosphonates as a Route to Enantiomeric Pure Aryl Alkyl or Dialkyl Sulfoxides.

-Titanium-catalyzed oxidation of the title thiomethylphosphonates (I) and (III) with tert-butyl or cumene hydroperoxide affords the corresponding sulfinylmethylphosphonates (II) and (IV) in excellent optical purity. Reaction of compounds (II) and (IV) with Grignard reagents proceeds smoothly to furnish dialkyl or aryl alkyl sulfoxides in high enantioselectivity and with inversion of the configuration as demonstrated for methyl phenyl sulfoxide (VI). -(CAPOZZI, MARIA ANNUNZIATA