One-pot transformation of p-toluenesulfonates of 2,3-epoxy alcohols into allyic alcohols

A convenient and efficient method for the synthesis of synthetically useful non-racemic allylic alcohols from 4-methylbenzenesulfonates of non-racemic 2,3-epoxy alcohols is described. Satisfactory yields are obtained by treatment of 4-methylbenzenesulfonates of non-racemic 2,3-epoxy alcohols with potassium iodide followed by zinc powder and ammonium chloride in a one-pot manner. The method has been successfully applied to the synthesis of a key building block of C 30 C 37 botryococcenes.