Effect of amines on the selective bromination of some β-substituted-2- butenoic esters

Abstract The effect of amines on the selective bromination of some β-substituted-2-butenoic esters is described. The bromination of methyl (Z)-4-t-butyldiphenylsilyloxy-3-methylbutenoate 2 in the presence of DIPEA (N, N-diisopropylethylamine) and the successive treatment of the obtained dibromide with potassium t-butoxide afford the desired Z bromide selectively. But the corresponding E bromide forms exclusively when 2, 6-di-t-butyl-4-methylpyridine is used in the bromination.