Ring-opening of 2,3-epoxy-1-propanol with R3Al: Unprecedented regiochemical switching simply achieved by changing alkyl substituents of aluminium reagent

Several control experiments were designed to optimize the reaction of 2,3-epoxy-1-propanol with R3Al (R = Me, Et or iBu) and to probe for the nature of aluminium-bound alkyl groups that influence the reactivity and selectivity. The reported studies revealed that the Et3Al mediated reaction leads to the C-2 product in contrast to the well-known C-3 substitution promoted by Me3Al.