Laboratory-synthesized (Z)-2,4-Enyne oxiranes were subjected iron-catalyzed reactions with Grignard reagents. The reactions afforded majorly E-configured vinylallenes with a hydroxyl group on the allylic carbon as the 1,5-(SN2'')-substitution products. However, in some case, along with the desired vinyllallenes products, 1,1- (SN2) and 1,3-substitution (SN2’) by-products were also recovered. Diastereo-selectivity of the method is strictly reliant on the syn/anti mode of the alkylation process. This study provides a new methodology for the synthesis of vinylallenes which are potential building blocks of biological active molecules.