Stereoselective synthesis of 1,4-dienes by chelation-controlled reduction of benzothiazole β-oxosulfides

Article abstract of DOI:10.1016/S0040-4039(98)00622-4

Allylated β-oxosulfides of benzothiazole can replace β-oxophosphane oxides to provide a stereospecific alkene synthesis. These sulfides, by reduction with sodium borohydride afford predominantly syn β-hydroxy sulfides. DIBAL reduction in the presence of magnesium bromide improves the syn stereomer formation. Base treatment of these β-hydroxy sulfides affords (Z)-allyl thiiranes which are converted into (E, Z)-dienes.