β‐ N ‐heterocyclic cyclobutane carboximides: synthesis through a tandem base‐catalyzed amidation/aza‐Michael addition protocol and facile transformations - CEA - Commissariat à l’énergie atomique et aux énergies alternatives Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2023

β‐ N ‐heterocyclic cyclobutane carboximides: synthesis through a tandem base‐catalyzed amidation/aza‐Michael addition protocol and facile transformations

Résumé

A stereoselective one‐pot double derivatization of cyclobutene‐1‐carboxylic acid via a mild organic base catalyzed amidation/aza‐Michael addition of benzo[d]oxazol‐2(3H)‐ones has been developed. This unprecedented tandem reaction provides access to novel β‐ N ‐heterocyclic cyclobutane carboximide derivatives with a trans geometry. The carboximide moiety reacts smoothly with nucleophiles, allowing access to diverse derivatives of trans ‐β‐ N ‐heterocyclic cyclobutanecarboxylic acid, including peptidomimetic structures.
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Dates et versions

cea-04453341 , version 1 (13-02-2024)

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Stefano Barranco, Federico Cuccu, Dayi Liu, Sylvie Robin, Régis Guillot, et al.. β‐ N ‐heterocyclic cyclobutane carboximides: synthesis through a tandem base‐catalyzed amidation/aza‐Michael addition protocol and facile transformations. European Journal of Organic Chemistry, 2023, 26 (16), pp.e202300183. ⟨10.1002/ejoc.202300183⟩. ⟨cea-04453341⟩
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