Stereoselective Synthesis of Racemic and Optically ActiveE-Vinyl andE-Dienyl Sulfoxides via Wittig Reaction of α-Sulfinyl Phosphonium Ylides

A series of α-sulfinyl phosphonium ylides have been obtained in the reaction of phosphonium mono- and diylides with sulfinic acid esters. The use of (−)-( S )-menthyl p -toluenesulfinate in this reaction afforded the corresponding ( S )-(( p -tolylsulfinyl)methyl)triphenylphosphonium ylide. The Wittig reaction of these ylides with saturated and unsaturated aldehydes resulted in the formation of racemic and optically active (+)-( R )-vinyl and dienyl sulfoxides with the E-geometry. The synthesis of (+)-( R )-(( p -tolylsulfinyl)methyl)triphenylphosphonium iodide as a precursor of the optically active ylide has also been described.