Regio- and Stereoselective Aminopentadienylation of Carbonyl Compounds
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Campo DC | Valor | Idioma |
---|---|---|
dc.contributor | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | es |
dc.contributor | Síntesis Asimétrica (SINTAS) | es |
dc.contributor.author | Bosque, Irene | - |
dc.contributor.author | Bagdatli, Emine | - |
dc.contributor.author | Foubelo, Francisco | - |
dc.contributor.author | Gonzalez-Gomez, Jose C. | - |
dc.contributor.other | Universidad de Alicante. Departamento de Química Orgánica | es |
dc.contributor.other | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | es |
dc.date.accessioned | 2014-05-22T12:31:30Z | - |
dc.date.available | 2014-05-22T12:31:30Z | - |
dc.date.issued | 2014-02-03 | - |
dc.identifier.citation | Journal of Organic Chemistry. 2014, 79(4): 1796-1804. doi:10.1021/jo402854z | es |
dc.identifier.issn | 0022-3263 (Print) | - |
dc.identifier.issn | 1520-6904 (Online) | - |
dc.identifier.uri | http://hdl.handle.net/10045/37266 | - |
dc.description.abstract | A simple and robust protocol is detailed for the preparation of enantioenriched α-substituted (1,4-pentadien-3-yl)amine derivatives. The methodology involves the addition of an in situ formed pentadienyl indium reagent to chiral tert-butylsulfinimines, previously formed in the same pot. The addition takes place with excellent γ-regio- and diastereoselectivity for a wide range of carbonyl compounds, including α-unsubstituted aldehydes and methyl alkyl ketones. The catalytic hydrogenation of the sulfinamines obtained provides a convenient access to chiral α-substituted (3-pentyl)amines. The hydroboration–oxidation of the α-(1,4-pentadien-3-yl)amine derivatives, followed by a cyclization under Mitsunobu conditions, takes place with an excellent diastereoselectivity governed by the chiral sulfinyl group. | es |
dc.description.sponsorship | We thank the Spanish Ministerio de Ciencia e Innovación (CTQ2011-24165) for financial support. I.B. acknowledges the Generalitat Valenciana for a predoctoral fellowship (ACIF/2011/159). E.B. acknowledges the Council of Higher Education- Turkey for a postdoctoral fellowship (16.10.12-B.09.6.YÖK.0.71.01-207.02-12285). | es |
dc.language | eng | es |
dc.publisher | American Chemical Society | es |
dc.rights | © 2014 American Chemical Society | es |
dc.subject | Carbonyl compounds | es |
dc.subject | Aminopentadienylation | es |
dc.subject.other | Química Orgánica | es |
dc.title | Regio- and Stereoselective Aminopentadienylation of Carbonyl Compounds | es |
dc.type | info:eu-repo/semantics/article | es |
dc.peerreviewed | si | es |
dc.identifier.doi | 10.1021/jo402854z | - |
dc.relation.publisherversion | http://dx.doi.org/10.1021/jo402854z | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.relation.projectID | info:eu-repo/grantAgreement/MICINN//CTQ2011-24165 | - |
Aparece en las colecciones: | INV - CESO - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
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2014_Bosque_etal_JOC_final.pdf | Versión final (acceso restringido) | 812,43 kB | Adobe PDF | Abrir Solicitar una copia |
2014_Bosque_etal_JOC.pdf | Versión revisada (acceso abierto) | 793,31 kB | Adobe PDF | Abrir Vista previa |
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