Tertiary Enamide-Promoted Diastereoselective Domino: N-Acyliminium Ion Trapping and Nazarov Cyclization.
Org Lett
; 22(17): 6771-6775, 2020 09 04.
Article
em En
| MEDLINE
| ID: mdl-32787267
ABSTRACT
N-Acyliminium ions generated from enamidyl vinyl ketones provided cyclopentenoid-fused diazepines diastereoselectively using BF3·Et2O in one pot through a domino N-acyliminium ion trapping/Nazarov reaction, simultaneously generating three new stereogenic centers. The particular structural design of the cross-conjugated dienone dictates the torquoselectivity observed in this polarized Nazarov reaction. Various N-bridgehead polycyclic scaffolds of putative pharmacological interest were obtained. Cyclic voltammetry was used to support the preferred reaction sequence within this domino reaction.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Lett
Ano de publicação:
2020
Tipo de documento:
Article