Pseudo-multicomponent 1,3-dipolar cycloaddition involving metal-free generation of unactivated azomethine ylides
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Title: | Pseudo-multicomponent 1,3-dipolar cycloaddition involving metal-free generation of unactivated azomethine ylides |
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Authors: | Belabbes, Asmaa | Retamosa, Maria de Gracia | Foubelo, Francisco | Sirvent, Ana | Nájera, Carmen | Yus, Miguel | Sansano, Jose M. |
Research Group/s: | Síntesis Asimétrica (SINTAS) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Pseudo-multicomponent | 1,3-dipolar cycloaddition | Metal-free generation | Unactivated azomethine ylides |
Issue Date: | 27-Jan-2023 |
Publisher: | Royal Society of Chemistry |
Citation: | Organic & Biomolecular Chemistry. 2023, 21: 1927-1936. https://doi.org/10.1039/D3OB00023K |
Abstract: | The pseudo-multicomponent reaction between propargyl amine, an aldehyde and an electron-deficient alkene is described. The C–H activation takes place thermally and allows the obtaining of cycloadducts in very good yields with high diastereoselectivities. The relative configuration is determined by X-ray diffraction analysis of the chiral molecule, obtained as a single diastereoisomer, using a chiral maleimide. A brief study of the stability of the possible ylides involved in the process is also mentioned, confirming the high diastereoselectivity observed. The high functional group density of these cycloadducts permits the synthesis of complex heterocycles. After allylation or propargylation of the pyrrolidine nitrogen atom, RCM-DA cycloaddition or cyclotrimerization with an alkyne is studied, respectively. In this last example, the resulting tetracyclic structures are of potential interest as drugs for the treatment of cystic fibrosis. |
Sponsor: | We gratefully acknowledge financial support from the Spanish Ministerio de Ciencia, Innovación y Universidades (project RED2018-102387-T) the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2017-82935-P and PID2019-107268GB-I00), the Generalitat Valenciana (IDIFEDER/2021/013, GVA-COVID19/2021/079 and CIDEGENT/2020/058), Medalchemy S.L. (Medalchemy-18T) and the University of Alicante (VIGROB-068, UAUSTI21-05). |
URI: | http://hdl.handle.net/10045/131882 |
ISSN: | 1477-0520 (Print) | 1477-0539 (Online) |
DOI: | 10.1039/D3OB00023K |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © Royal Society of Chemistry 2023 |
Peer Review: | si |
Publisher version: | https://doi.org/10.1039/D3OB00023K |
Appears in Collections: | INV - SINTAS - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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Belabbes_etal_2023_OrgBiomolChem_accepted.pdf | Accepted Manuscript (acceso abierto) | 1,13 MB | Adobe PDF | Open Preview |
Belabbes_etal_2023_OrgBiomolChem_final.pdf | Versión final (acceso restringido) | 623,65 kB | Adobe PDF | Open Request a copy |
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