-Phosphoryl sulfoxides. X. A general synthesis of optically active α-chlorovinyl sulfoxides

Article abstract of DOI:10.1016/S0957-4166(96)00458-2

A general and efficient synthesis of enantiomeric α-chlorovinyl p-tolyl sulfoxides 1 using (+)-(S)(C)(S)(S)-α-chloro-α-dimethoxyphosphorylmethyl p-tolyl sulfoxide as a key substrate for the Horner-Wittig reaction with carbonyl compounds is described. The E/Z ratio of geometrical isomers of 1 was determined and briefly investigated: The X-ray diffraction structures of (Z)-1-chloro-1-p-tolylsulfinyl-2-phenyl-ethene and (Z)-1-chloro-1-p-tolylsulfinyl-2-(2-thienyl)-ethene are reported.