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Synthesis of N ‐Aryl‐2‐allylpyrrolidines via Palladium‐Catalyzed Carboamination Reactions of γ‐( N ‐Arylamino)alkenes with Vinyl Bromides
Author(s) -
Ney Joshua E.,
Hay Michael B.,
Yang Qifei,
Wolfe John P.
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505172
Subject(s) - chemistry , aryl , vinyl bromide , alkene , pyrrolidine , bromide , catalysis , medicinal chemistry , organic chemistry , indoline , palladium , alkyl
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.