Synthesis of N-Aryl-2-allyl Pyrrolidines via Palladium-catalyzed Carboamination Reactions of γ-(N-Arylamino)alkenes with Vinyl Bromides.
Adv Synth Catal
; 347(11-13): 1614-1620, 2005 Oct 01.
Article
em En
| MEDLINE
| ID: mdl-20221320
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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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Adv Synth Catal
Ano de publicação:
2005
Tipo de documento:
Article