Article Dans Une Revue Molecules Année : 2020

Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study

Résumé

Inversions in the periselectivity of formal aza-Diels-Alder cycloadditions between ↵-oxoketenes generated by a thermally-induced Wol↵ rearrangement and 1-azadienes were observed experimentally as a function of the ↵-oxoketene and the 1-azadiene, as well as the reaction temperature and time. Some unexpected inversion in the diastereoselectivity was observed, too. These variations in selectivities were fully rationalized by computational modeling using density functional theory (DFT) methods.

Domaines

Fichier principal
Vignette du fichier
pub-2020Mol-4811bis.pdf (2.23 Mo) Télécharger le fichier
Origine Fichiers produits par l'(les) auteur(s)
Licence
Loading...
HAL

Est décrite par hal-02990562 Image Marc Presset, Michel Rajzmann, Guillaume Dauvergne, Jean Rodriguez, Yoann Coquerel. Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study. Illustration. France. 2020. ⟨hal-02990562⟩

Dates et versions

hal-02990656 , version 1 (17-11-2020)

Licence

Identifiants

Citer

Marc Presset, Michel Rajzmann, Guillaume Dauvergne, Jean Rodriguez, Yoann Coquerel. Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study. Molecules, 2020, Diels-Alder Reaction in Organic Synthesis, 25 (20), pp.4811. ⟨10.3390/molecules25204811⟩. ⟨hal-02990656⟩
97 Consultations
110 Téléchargements

Altmetric

Partager

  • More