| Título: | Binap-gold (I) versus Binap-silver trifluoroacetate complexes as catalysts in 1,3-dipolar cycloadditions of axomethine ylides |
| Autores: |
Martín Rodríguez, María Nájera Domingo, Carmen Sansano Gil, José Miguel Cózar Ruano, Abel de Cossío Mora, Fernando Pedro |
| Fecha: |
2011-12-19 2011-12-19 2011 2011-12-09 |
| Publicador: | RUA Docencia |
| Fuente: |
 |
| Tipo: | info:eu-repo/semantics/article |
| Tema: |
Asymmetric synthesis Azomethine Cycloaddition Gold Silver Química Orgánica |
| Descripción: |
The 1,3-dipolar cycloaddition between azomethine ylides and alkenes is efficiently catalysed by [{(Sa)-Binap-Au(tfa)}2] (Binap=2,2′-bis(diphenylphosphino)-1,1′-binaphthyl; tfa=trifluoroacetyl). Maleimides, 1,2-bis(phenylsulfonyl)ethylene, chalcone and nitrostyrene were suitable dipolarophiles even when using sterically hindered 1,3-dipole precursors. The results obtained in these transformations improve the analogous ones obtained in the same reactions catalysed by [Binap–Ag(tfa)]. In addition, computational studies have also been carried out to demonstrate both the high enantioselectivity exhibited by the chiral gold(I) complex, and the non-linear effect observed in this transformation. This work has been supported by the DGES of the Spanish Ministerio de Ciencia e Innovación (MICINN) (Consolider Ingenio 2010 CSD2007-00006, FEDER-CTQ2007-62771/BQU, CTQ2007/67528, CTQ2010-20387 and by the Hispano-Brazilian project PHB2008-0037-PC), Generalitat Valenciana (PROMETEO/2009/039), the Basque government (grant IT-324-07) and by the University of Alicante. |
| Idioma: | Inglés |
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