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. 2005 Oct 1;347(11-13):1614-1620.
doi: 10.1002/adsc.200505172.

Synthesis of N-Aryl-2-allyl Pyrrolidines via Palladium-catalyzed Carboamination Reactions of γ-(N-Arylamino)alkenes with Vinyl Bromides

Joshua E Ney  1 , Michael B Hay, Qifei Yang, John P Wolfe
Affiliations

Synthesis of N-Aryl-2-allyl Pyrrolidines via Palladium-catalyzed Carboamination Reactions of γ-(N-Arylamino)alkenes with Vinyl Bromides

Joshua E Ney et al. Adv Synth Catal. .

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.

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Figures

Scheme 1
Scheme 1
Proposed mechanism of carboamination reaction.
Scheme 2
Scheme 2
Proposed mechanism for formation of regioisomer 4.
Scheme 3
Scheme 3
Proposed mechanism for formation of 5.
See this image and copyright information in PMC

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