1.
J Org Chem
; 80(14): 7158-71, 2015 Jul 17.
Artigo
em Inglês
| MEDLINE
| ID: mdl-26086789
RESUMO
The γ-functionalization of oxindoles bearing nonsymmetric 3-alkylidene groups via vinylogous Michael-type addition to nitroolefins was realized. The suppression of the interconversion between the E and Z isomers of the starting oxindoles allowed a site-specific diastereoselective and enantioselective transformation. Specific experiments allowed us to establish the rate-determining step of the reaction and to advance a robust hypothesis for the exclusive formation of an s-cis enolate as the only reactive intermediate.