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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.

Organolithium or Heck type cyclization of N-ortho-iodobenzyl-2-alkenylpyrrolidines to give indolizidines