(E)-N-isopropyl-3-tosylacrylamide: A new α-acylvinyl cation equivalent in the synthesis of α-substituted acrylamides

Article abstract of DOI:10.1016/S0040-4039(01)93861-4

The reaction of (E)-N-isopropyl-3-tosylacrylamide with different Grignard reagents leads after hydrolysis to the corresponding α-alkylated systems, which by treatment with methanolic potassium hydroxide yield the expected α-methylene amides. In the case of using vinylmagnesium bromide the aqueous hydrolysis after the first step affords directly mikanecic acid diisopropylamide. When sodium diethyl malonate is used as nucleophile the corresponding succinimide derivatives 13 and 14 are isolated.