Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study - MédiHAL Accéder directement au contenu
Image (Illustration) 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 α-oxoketenes generated by a thermally-induced Wolff rearrangement and 1-azadienes were observed experimentally as a function of the α-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

Chimie organique

Dates et versions

hal-02990562 , version 1 (05-11-2020)

Licence

Domaine public

Identifiants

  • HAL Id : hal-02990562 , version 1

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. Illustration. France. 2020. ⟨hal-02990562⟩
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