ARKIVOC

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

O García-Calvo, N Sotomayor, E Lete, I Coldham

Index: Garcia-Calvo, Oihane; Sotomayor, Nuria; Lete, Esther; Coldham, Iain Arkivoc, 2011 , vol. 2011, # 5 p. 57 - 66

Full Text: HTML

Citation Number: 1

Abstract

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