Diastereoselective Synthesis of Nitropyrrolizidines from Enantiopure exo- 4-Nitro-3,5-diphenylproline through 1,3-Dipolar Cycloadditions of non- Stabilized Azomethine Ylides
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Campo DC | Valor | Idioma |
---|---|---|
dc.contributor | Síntesis Asimétrica (SINTAS) | es_ES |
dc.contributor.author | García-Mingüens, Eduardo | - |
dc.contributor.author | Nájera, Carmen | - |
dc.contributor.author | Sansano, Jose M. | - |
dc.contributor.other | Universidad de Alicante. Departamento de Química Orgánica | es_ES |
dc.contributor.other | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | es_ES |
dc.date.accessioned | 2018-04-20T11:35:13Z | - |
dc.date.available | 2018-04-20T11:35:13Z | - |
dc.date.issued | 2018 | - |
dc.identifier.citation | Letters in Organic Chemistry. 2018, 15(5): 431-440. doi:10.2174/1570178615666171221142214 | es_ES |
dc.identifier.issn | 1570-1786 (Print) | - |
dc.identifier.issn | 1875-6255 (Online) | - |
dc.identifier.uri | http://hdl.handle.net/10045/74910 | - |
dc.description.abstract | Enantiopure exo-4-nitro-3,5-diphenylproline reacts with aldehydes and electrophilic alkenes, in good yields, through a multicomponent 1,3-dipolar cycloaddition where the intermediate azomethine ylide is generated by the decarboxylative route. The reactions with maleimides afford diastereoselectively nitropyrrolizidines. Dimethyl fumarate and 1,2-bis(phenylsulfonyl)ethylene also give variable mixtures of diastereoisomeric nitropyrrolizidines. The replacement of aldehydes by phenyl-3-buten-2- one also affords satisfactory results with high diastereoselection although in lower yields. The stereochemical outcome is studied and defined according to the absolute configuration of the resulting cycloadducts. | es_ES |
dc.description.sponsorship | We gratefully acknowledge financial support from the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEO2009/039 and PROMETEOII/2014/ 017) and the University of Alicante. | es_ES |
dc.language | eng | es_ES |
dc.publisher | Bentham Science Publishers | es_ES |
dc.rights | © 2018 Bentham Science Publishers | es_ES |
dc.subject | Pyrrolizidine | es_ES |
dc.subject | Nitroprolinates | es_ES |
dc.subject | Cycloaddition | es_ES |
dc.subject | Azomethine ylides | es_ES |
dc.subject | Decarboxylation | es_ES |
dc.subject | Multicomponent | es_ES |
dc.subject.other | Química Orgánica | es_ES |
dc.title | Diastereoselective Synthesis of Nitropyrrolizidines from Enantiopure exo- 4-Nitro-3,5-diphenylproline through 1,3-Dipolar Cycloadditions of non- Stabilized Azomethine Ylides | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.peerreviewed | si | es_ES |
dc.identifier.doi | 10.2174/1570178615666171221142214 | - |
dc.relation.publisherversion | https://doi.org/10.2174/1570178615666171221142214 | es_ES |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es_ES |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas |
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2018_Garcia-Minguens_etal_LettOrgChem_accepted.pdf | Accepted Manuscript (acceso abierto) | 2,57 MB | Adobe PDF | Abrir Vista previa |
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