Silver-Catalyzed Vinylcarbene Insertion into C-C Bonds of 1,3-Diketones with Vinyl-N-triftosylhydrazones.
Org Lett
; 24(44): 8136-8141, 2022 Nov 11.
Article
em En
| MEDLINE
| ID: mdl-36314934
ABSTRACT
We describe the silver-catalyzed formal insertion of a vinylcarbene into unstrained C(CO)-C bonds of 1,3-diketones using vinyl-N-triftosylhydrazones as vinylcarbene precursors. This method allows the rapid synthesis of otherwise inaccessible 2-vinyl-substituted 1,4-diketones from relatively simple substrates. This mild catalytic protocol exhibits a good functional group tolerance and substrate scope and allows for good chemoselectivity control. The preliminary theoretical calculations suggest that the reaction proceeds through a stepwise enol cyclopropanation/retro-aldol pathway.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article