Studies directed toward the synthesis of conformationally restricted neurotransmitter analogs: The addition of N-hydroxyimides to ethyl propiolate

N-Hydroxyimides were found to add readily to ethyl propiolate to yield the imidooxyacrylates in both protic and aprotic solvents. The trans isomer only was formed in aprotic solvents while both isomers were formed in protic solvents.