Abstract Carbolithiation reactions of 2-alkenyl-substituted pyrrolidines have been studied. An electronwithdrawing group in the alkene (R= CONEt2) is required for the 6-exo-trig cyclization to afford hexahydropyrrolo [1, 2-b] isoquinolines. Alternatively, the cyclization of the unactivated alkene can be performed under Heck conditions. Keywords: Organolithium, carbanion, carbolithiation, palladium, Heck, heterocycles