Selected Reaction of (Z)-Dimethyl α-(Bromomethyl) Fumarate with Secondary Amines

Abstract

Regioselective reaction of (Z)-dimethyl α-(bromomethyl) fumarate 2 with bulky secondary amines in ether as solvent at room temperature, leads exclusively to the rearranged substitution α-(functional alkyl amino) acrylic esters 4a-i in high yields. The less and more bulky amine gives rise respectively to the two successive (S_N2′) and (S_N2) substitution derivatives 5j,k and 51.