Transformation of epoxides into halohydrins and aminoalcohols by metal halides

Abstract

This work focuses on the development of an efficient procedure for the selective ring opening of substituted epoxides under mild and rapid conditions utilized either chromium(III) chloride or chromium(III) nitrate. The ring opening of alkyl- and aryl-substituted epoxides with these chromium(III) reagents produced halohydrin and aminoalcohol in high to excellent yield. Regioselectivity for a C-O bond cleavage of epoxide via Lewis acid promoted was greatly depended on the substitution pattern of epoxides furnished halohydrins and aminoalcohols through a predominantly SN2-type mechanism. This procedure is very simple, mild, rapid, commercially available, inexpensive, insensitive to air and high selectivity of product compared to those catalyzed by other Lewis acids.