A novel sulfinylation of alkenes by tosyl cyanide with titanium(IV) chloride

Article abstract of DOI:10.1016/S0040-4039(99)00894-1

Tosyl cyanide is activated by titanium(IV) chloride to generate a tolylsulfinyl chloride equivalent, which readily stereo- and regio- specifically adds to certain alkenes to provide β-chlorosulfoxides. These chlorides rapidly hydrolyse on silica gel to provide β-hydroxysulfoxides in stereocontrolled manner.