906800-35-9Relevant academic research and scientific papers
Synthesis of N-aryl-2-allylpyrrolidines via palladium-catalyzed carboamination reactions of γ-(N-arylamino)alkenes with vinyl bromides
Ney, Joshua E.,Hay, Michael B.,Yang, Qifei,Wolfe, John P.
, p. 1614 - 1620 (2005)
A palladium-catalyzed carboamination reaction of γ-N-arylamino alkenes with vinyl bromides that affords N-aryl-2-allyl pyrrolidines is described. These reactions proceed with high diastereoselectivity for the formation of trans-2,3- and cis-2,5-disubstituted pyrrolidines. Conditions for a tandem N-arylation/ carboamination sequence that leads to the formation of an N-aryl-2-allyl pyrrolidine or indoline via the coupling of a primary γ-amino alkene, an aryl bromide, and a vinyl bromide are also reported. The mechanism of the carboamination reactions and the origin of unexpected products that formally derive from rearrangement of the vinyl bromide are discussed.
