Diastereoselective ZnCl2-Mediated Joullié–Ugi Three-Component Reaction for the Preparation of Phosphorylated N-Acylaziridines from 2H-Azirines
dc.contributor.author | Allende, Julene | |
dc.contributor.author | Olaizola Alvarez, Yurre | |
dc.contributor.author | Ochoa de Retana Mendibil, Ana María | |
dc.contributor.author | Palacios, Francisco | |
dc.contributor.author | De los Santos Ruiz, Jesús Manuel | |
dc.date.accessioned | 2024-03-27T17:47:39Z | |
dc.date.available | 2024-03-27T17:47:39Z | |
dc.date.issued | 2024-02-27 | |
dc.identifier.citation | Molecules 29(5) : (2024) // Article ID 1023 | es_ES |
dc.identifier.issn | 1420-3049 | |
dc.identifier.uri | http://hdl.handle.net/10810/66527 | |
dc.description.abstract | We disclose a direct approach to the diastereoselective synthesis of phosphorus substituted N-acylaziridines based on a one-pot ZnCl2-catalyzed Joullié–Ugi three-component reaction of phosphorylated 2H-azirines, carboxylic acids and isocyanides. Hence, this robust protocol offers rapid access to an array of N-acylaziridines in moderate-to-good yields and up to 98:2 dr for substrates over a wide scope. The relevance of this synthetic methodology was achieved via a gram-scale reaction and the further derivatization of the nitrogen-containing three-membered heterocycle. The diastereo- and regioselective ring expansion of the obtained N-acylaziridines to oxazole derivatives was accomplished in the presence of BF3·OEt2 as an efficient Lewid acid catalyst. | es_ES |
dc.description.sponsorship | This research was funded by the Ministerio de Ciencia, Innovación y Universidades (MCIU–Madrid) (PID2021-122558OB-I00, UE) and Gobierno Vasco (GV, IT1701-22; UPV-EHU). | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | MDPI | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/PID2021-122558OB-I00 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/es/ | |
dc.subject | N-acylaziridine | es_ES |
dc.subject | 2H-azirine | es_ES |
dc.subject | Joullié–Ugi reaction | es_ES |
dc.subject | oxazol derivatives | es_ES |
dc.title | Diastereoselective ZnCl2-Mediated Joullié–Ugi Three-Component Reaction for the Preparation of Phosphorylated N-Acylaziridines from 2H-Azirines | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.date.updated | 2024-03-12T16:38:16Z | |
dc.rights.holder | © 2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/ 4.0/). | es_ES |
dc.relation.publisherversion | https://www.mdpi.com/1420-3049/29/5/1023 | es_ES |
dc.identifier.doi | 10.3390/molecules29051023 | |
dc.departamentoes | Química orgánica I | |
dc.departamentoeu | Kimika organikoa I |
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Except where otherwise noted, this item's license is described as © 2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/ 4.0/).