Synthesis of N‐Aryl‐2‐allylpyrrolidines via Palladium‐Catalyzed Carboamination Reactions of γ‐(N‐Arylamino)alkenes with Vinyl Bromides
- 19 October 2005
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 347 (11-13) , 1614-1620
- https://doi.org/10.1002/adsc.200505172
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.Keywords
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