Stereoselective synthesis of fissoldhimine alkaloid analogues via sequential electrooxidation and heterodimerization of ureas - Archive ouverte HAL
Article Dans Une Revue Chemical Communications Année : 2024

Stereoselective synthesis of fissoldhimine alkaloid analogues via sequential electrooxidation and heterodimerization of ureas

Résumé

This study develops a biogenetic synthesis strategy using electrooxidation and heterodimerization of N-substituted pyrrolidine-1-carboxamides to create diverse analogues of the fissoldhimine alkaloid core. Under acidic conditions, 2-alkoxypyrrolidine-1-carboxamides from Shono oxidation formed endo-heterodimers with high yields and diastereoselectivity. Enantioselective heterodimerization using chiral phosphoric acid catalysis produced exo-heterodimers with high enantioselectivity.

Domaines

Chimie organique
Fichier principal
Vignette du fichier
2024-ChemComm fissold.pdf (1.23 Mo) Télécharger le fichier
Origine Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-04733253 , version 1 (11-10-2024)

Identifiants

Citer

Emma Naulin, Aurélien Brion, Didine Biatuma, Emmanuel Roulland, Grégory Genta-Jouve, et al.. Stereoselective synthesis of fissoldhimine alkaloid analogues via sequential electrooxidation and heterodimerization of ureas. Chemical Communications, 2024, 60 (81), pp.11560-11563. ⟨10.1039/D4CC02616K⟩. ⟨hal-04733253⟩
12 Consultations
13 Téléchargements

Altmetric

Partager

More