| Título: | Synthesis of prolines by enantioselective 1,3-dipolar cycloaddition of azomethine ylides and alkenes catalyzed by chiral phosphoramidite-silver(I) complexes |
| Autores: |
Nájera Domingo, Carmen Retamosa Hernández, María de Gracia Martín Rodríguez, María Sansano Gil, José Miguel Cózar Ruano, Abel de Cossío Mora, Fernando Pedro |
| Fecha: |
2009-11-12 2009-11-12 2009 2009-09-28 |
| Publicador: | RUA Docencia |
| Fuente: |
 |
| Tipo: | info:eu-repo/semantics/article |
| Tema: |
Asymmetric catalysis Cycloaddition Azomethine ylides Silver Phosphorus Química Orgánica |
| Descripción: |
The endo-diastereo- and enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes is efficiently catalysed by chiral phosphoramidite-silver(I) perchlorate complexes. The reaction allows the presence of different types of substituents in the 1,3-dipole and can be applied to the synthesis of enantiomerically enriched, highly substituted prolines. This methodology was applied to the total synthesis of the inhibitors of the hepatitis C virus (HCV). Computational studies support a two-step mechanism predicting exactly the experimental results and the origin of both the diastereo- and enantioselections, as well as a reasonable explanation concerning the different reaction rates observed for some substrates. This work was supported by the DGES of the Spanish Ministerio de Educación y Ciencia (MEC) (Consolider INGENIO 2010 CSD2007-00006, CTQ2007-62771/BQU and CTQ2004-00808/BQU) and by the University of Alicante. |
| Idioma: | Inglés |
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