Polyene cyclization promoted by the cross-conjugated alpha-carbalkoxy enone system. Observation on a putative 1,5-hydride/1,3-alkyl shift under Lewis acid catalysis.
Org Lett
; 10(1): 121-3, 2008 Jan 03.
Article
em En
| MEDLINE
| ID: mdl-18052186
ABSTRACT
Polyene cyclization of compounds 3 and 4 under catalysis with AlCl3 and/or SnCl4 gave rise to complex bicyclic products 8 and 9, structures of which were highly unexpected, and X-ray analyses were invoked for unambiguously structural identification. Mechanistically, a tandem sigma-bond rearrangement process, including an unusual through-space 1,5-hydride or 1,3-alkyl shift as a key operation, is proposed.
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01-internacional
Base de dados:
MEDLINE
Assunto principal:
Alcenos
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Cetonas
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2008
Tipo de documento:
Article