Selective synthesis of cis-α,β-unsaturated sulfoxides and sulfides by the Horner-Wittig reaction with bis(2,2,2-trifluoroethyl)phosphono sulfoxides and aromatic aldehydes

Article abstract of DOI:10.1055/s-1996-4268

cis-α,β-Unsaturated sulfoxides were predominantly formed in the Horner-Wittig reaction with bis(2,2,2-trifluoroethyl)phosphono sulfoxides and aromatic aldehydes, while the reaction of the corresponding sulfides showed trans- or lower cis-selectivity. The reduction of cis-α,β-unsaturated sulfoxides with tributylphosphine in carbon tetrachloride gave cis-vinyl sulfides with retention of stereochemistry.