The rearrangement of gamma-chloro, beta-hydroxy or beta-vinyl N-allyl-N-benzyl-alpha,alpha-dichlorocarboxyamides to gamma-aminobutyric acid analogues is efficiently promoted by CuCl\N,N,N',N'-tetramethylethylendiamine. With the beta-vinyl functionalization a tandem radical-radical reaction, yielding 3-aza-2-oxo-bicyclo[3,3,0]octane adducts, is also observed.
Rearrangement of N-allyl-alpha,alpha-dichloroamides, beta- or gamma-functionalized, to substituted analogues of the gamma-aminobutyric acid (GABA) / Bellesia, Franco; Forti, Luca; Ghelfi, Franco; G., Ghirardini; Libertini, Emanuela; Pagnoni, Ugo Maria; Pinetti, Adriano; N., Prochilo. - In: SYNTHETIC COMMUNICATIONS. - ISSN 0039-7911. - STAMPA. - 29:(1999), pp. 3739-3748. [10.1080/00397919908086013]
Rearrangement of N-allyl-alpha,alpha-dichloroamides, beta- or gamma-functionalized, to substituted analogues of the gamma-aminobutyric acid (GABA)
BELLESIA, Franco;FORTI, Luca;GHELFI, Franco;LIBERTINI, Emanuela;PAGNONI, Ugo Maria;PINETTI, Adriano;
1999
Abstract
The rearrangement of gamma-chloro, beta-hydroxy or beta-vinyl N-allyl-N-benzyl-alpha,alpha-dichlorocarboxyamides to gamma-aminobutyric acid analogues is efficiently promoted by CuCl\N,N,N',N'-tetramethylethylendiamine. With the beta-vinyl functionalization a tandem radical-radical reaction, yielding 3-aza-2-oxo-bicyclo[3,3,0]octane adducts, is also observed.
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