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

Copper-catalyzed intramolecular hydroamination of allenylamines to 3-pyrrolines or 2-alkenylpyrrolidines

[Tsuhako, Akiko; Oikawa, Daisuke; Sakai, Kazushi; Okamoto, Sentaro Tetrahedron Letters, 2008 , vol. 49, # 46 p. 6529 - 6532]

Palladium-Catalyzed Reactions of N-Allylbenzotriazoles with Amines: Intramolecular Allylamination Routes to 2-Vinylpyrrolidines and 2-Vinylpiperidines

[Katritzky, Alan R.; Yao, Jiangchao; Yang, Baozhen Journal of Organic Chemistry, 1999 , vol. 64, # 16 p. 6066 - 6070]

Synthesis of functionalised azecine and azonine derivatives via an enolate assisted aza Claisen rearrangement

[Bremner, John B.; Perkins, David F. Tetrahedron, 2005 , vol. 61, # 10 p. 2659 - 2665]