N-Alkoxyacrylamides in Domino Reactions: Catalytic and Stereoselective Access to δ-Lactams

Philippe Champetter , Omar Castillo-Aguilera , Catherine Taillier (1) , Jean-François Brière (2) , Vincent Dalla (1) , Sylvain Oudeyer (2) , Sébastien Alain Comesse

1 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

The use of N‐alkoxyacrylamides in a domino aza‐Michael/intramolecular‐Michael reaction for the synthesis of δ‐lactams is presented. This base‐catalyzed process operates under mild conditions and the polysubstituted aza‐heterocycles are isolated in good yields with good to excellent stereocontrol. The first domino aza‐Michael/intramolecular‐Michael reaction employing acrylamides as key ambivalent partners for the synthesis of δ‐lactams is presented. It has been shown that the desired reactivity is contingent to the presence of an N‐alkoxy group within the acrylamides. Thus, in a base‐catalyzed process that operates under mild conditions, N‐alkoxyacrylamides are readily converted into polysubstituted δ‐lactams in good yields with good to excellent stereocontrol.

Domaines: Chimie; Catalyse; Chimie organique

Philippe Champetter, Omar Castillo-Aguilera, Catherine Taillier, Jean-François Brière, Vincent Dalla, et al.. N-Alkoxyacrylamides in Domino Reactions: Catalytic and Stereoselective Access to δ-Lactams. European Journal of Organic Chemistry, 2019, 47, pp.7703-7710. ⟨10.1002/ejoc.201901528⟩. ⟨hal-02376720⟩