Probing N-Alkoxy Effects in Domino Reactions of α-Bromoacetamide Derivatives Towards Functionalized γ-Lactams

Philippe Champetter (1) , Ismail Alahyen (1) , Catherine Taillier (1) , Jean-François Brière (2) , Vincent Dalla (1) , Sylvain Oudeyer (2) , Sébastien Comesse (1)

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

The main objective of the present work is to better delineate the positive impact of N-alkoxy versus N-alkyl moieties in domino reactions. The key role of the metallic counterion of the basic reagent via a templating effect has been established, giving an insight over the superiority of N-alkoxy α-bromoacetamides compared to their N-alkyl analogues. The former demonstrated enhanced reactivity and efficiency, thus equiring milder conditions and leading to a wider scope of γ-lactams in good to excellent yields ranging from 67 to 98%. Overall, this study contributes to the emerging point of view that Nalkoxy nitrogenated compounds are useful building blocks with powerful but still under-developed synthetic potential, in particular in domino reactions.

Mots clés: domino reactions; N-alkoxyacrylamides; stereoselective synthesis; γ-lactams; reactivity

Domaines: Chimie organique

Philippe Champetter, Ismail Alahyen, Catherine Taillier, Jean-François Brière, Vincent Dalla, et al.. Probing N-Alkoxy Effects in Domino Reactions of α-Bromoacetamide Derivatives Towards Functionalized γ-Lactams. ChemistrySelect, 2022, 7 (38), ⟨10.1002/slct.202203305⟩. ⟨hal-03808493⟩