Remote Asymmetric Oxa-Diels-Alder Reaction of 5-Allylic Furfurals via Dearomatizative Tetraenamine Catalysis.
Org Lett
; 20(3): 804-807, 2018 02 02.
Article
em En
| MEDLINE
| ID: mdl-29355329
ABSTRACT
A previously unreported activation mode is developed through the generation of dearomatizative tetraenamine species between 5-allylic furfurals and a bifunctional amine-thiourea catalyst. The very remote ζ,η-alkenes perform as effective HOMO-raised dienophiles in inverse-electron-demand oxa-Diels-Alder cycloadditions with isatin-derived oxadiene substrates, delivering multifunctional spirocyclic oxindoles incorporating a dihydropyran skeleton in moderate to high yields with good to excellent enantio- and diastereoselectivity.
Texto completo:
1
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article