Allyl alcohol, reactions isothiocyanate

By sequential treatment of the sodium alkoxides of allylic alcohols with an equimolar amount of an alkyl isothiocyanate, allylic thiocarbonimidates are obtained. These compounds undergo cyclization induced by iodine in tetrahydrofuran, or bis(collidine)bromonium perchlorate in dichloromethane, to give the corresponding Al-alkyl-2-oxazolidinones, precursors of amino alcohols, in good yield. The cyclization of thiocarbonimidates prepared from 2-cyclohexenols proceeded with total regio- and stereoselectivity and a single diastereomer was recovered from the reaction mixture138 140. 

---