β-N-Heterocyclic Cyclobutane Carboximides: Synthesis through a Tandem Base-Catalyzed Amidation/aza-Michael Addition Protocol and Facile Transformations
Barranco S.;Secci F.;Caboni P.;Frongia A.
2023-01-01
Abstract
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.File | Dimensione | Formato | |
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Eur J Org Chem - 2023 - Barranco - ‐N‐Heterocyclic Cyclobutane Carboximides Synthesis through a Tandem Base‐Catalyzed.pdf Solo gestori archivio
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Accepted article.docx Open Access dal 21/04/2024
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