title: Synthesis of N-Aryl-2-allyl Pyrrolidines via Palladium-catalyzed Carboamination Reactions of γ-(N-Arylamino)alkenes with Vinyl Bromides.
abstract: 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.
authors.affiliation: University of Michigan, Department of Chemistry 930 N. University Ave, Ann Arbor, Michigan, 48109-1055, USA.
authors.forename: Joshua E
authors.initials: JE
authors.lastname: Ney
authors.forename: Michael B
authors.initials: MB
authors.lastname: Hay
authors.forename: Qifei
authors.initials: Q
authors.lastname: Yang
authors.forename: John P
authors.initials: JP
authors.lastname: Wolfe