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.
Domaines
Physique [physics]
Fichier principal
Eur J Org Chem - 2023 - Barranco - ‐N‐Heterocyclic Cyclobutane Carboximides Synthesis through a Tandem Base‐Catalyzed.pdf (2.13 Mo)
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