Rearrangement of N-allyl-alpha,alpha-dichloroamides, beta- or gamma-functionalized, to substituted analogues of the gamma-aminobutyric acid (GABA)

Authors
Bellesia, F Forti, L Ghelfi, F Ghirardini, G Libertini, E Pagnoni, UM Pinetti, A Prochilo, N
Citation
F. Bellesia et al., Rearrangement of N-allyl-alpha,alpha-dichloroamides, beta- or gamma-functionalized, to substituted analogues of the gamma-aminobutyric acid (GABA), SYN COMMUN, 29(21), 1999, pp. 3739-3748
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
21
Year of publication
1999
Pages
3739 - 3748
Database
ISI
SICI code
0039-7911(1999)29:21<3739:RONBOG>2.0.ZU;2-O
Abstract
The rearrangement of gamma-chloro, beta-hydroxy or beta-vinyl N-allyl-N-ben zyl-alpha,alpha-dichlorocarboxyamides to gamma-aminobutyric acid analogues is efficiently promoted by CuCl\N,N,N',N'-tetramethylethylendiamine. With t he beta-vinyl functionalization a tandem radical-radical reaction, yielding 3-aza-2-oxo-bicyclo[3,3,0]octane adducts, is also observed.