alpha-phosphoryl sulfoxides .10. A general synthesis of optically active alpha-chlorovinyl sulfoxides

A general and efficient synthesis of enantiomeric alpha-chlorovinyl p-tolyl sulfoxides 1 using (+)-(S)(C)(S)(S)-alpha-chloro-alpha-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. Copyright (C) 1996 Elsevier Science Ltd.