Boronic Acid Catalyzed Regioselective Aminolysis of 3,4-Epoxy Alcohols

A C-3 aminolysis of epoxy homoallylic alcohols has been accomplished, which was catalyzed by a commercially available boronic acid. Due to the directing effect of the hydroxyl moiety, the ring opening reaction of a variety of 3,4-epoxy alcohols bearing different substitution patterns with various aromatic amines as nucleophiles proceeded in a stereospecific reaction pathway at the C-3 position furnishing various amino alcohols as products in a highly regioselective manner