Binap-silver salts as chiral-catalysts for the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and alkenes
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| Title: | Binap-silver salts as chiral-catalysts for the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and alkenes |
|---|---|
| Authors: | Mancebo Aracil, Juan | Martín Rodríguez, María | Nájera, Carmen | Sansano, Jose M. | Costa, Paulo R.R. | Lima, Evanoel Crizanto de | Dias, Ayres G. |
| Research Group/s: | Procesos Catalíticos en Síntesis Orgánica |
| Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica |
| Keywords: | Enantioselective | Azomethine |
| Knowledge Area: | Química Orgánica |
| Date Created: | Oct-2012 |
| Issue Date: | 15-Dec-2012 |
| Publisher: | Elsevier |
| Citation: | MANCEBO-ARACIL, Juan, et al. "Binap-silver salts as chiral-catalysts for the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and alkenes". Tetrahedron: Asymmetry. Vol. 23, No. 22-23 (15 Dec. 2012). ISSN 0957-4166, pp. 1596-1606 |
| Abstract: | Binap-AgSbF6 catalyzed 1,3-dipolar cycloadditions between azomethine ylides and electrophilic alkenes are described and compared with analogous transformations mediated by other Binap-silver(I) salt complexes. Maleimides and 1,2-bis(phenylsulfonyl)ethylene are suitable dipolarophiles for obtaining very good enantioselectivities, even better values are generated by a multicomponent version. There are some very interesting applications of the disulfonylated cycloadducts in the total synthesis of cis-2,5-disubstituted pyrrolidines, precursors of natural products, or valuable intermediates in the synthesis of antiviral compounds. |
| Sponsor: | This work has been supported by the Spanish Ministerio de Ciencia e Innovación (MICINN) through the Hispano-Brazilian project PHB2008-0037-PC and CNPq-2878, Consolider INGENIO 2010 CSD2007-00006, CTQ2010-20387, FEDER, Generalitat Valenciana (PROMETEO/2009/039), and by the University of Alicante. MM-R thanks MEC for a predoctoral fellowship. EC thanks CNPq for a predoctoral Doutorado Sanduíche stay. |
| URI: | http://hdl.handle.net/10045/25420 |
| ISSN: | 0957-4166 (Print) | 1362-511X (Online) |
| DOI: | 10.1016/j.tetasy.2012.10.015 |
| Language: | eng |
| Type: | info:eu-repo/semantics/article |
| Peer Review: | si |
| Publisher version: | http://dx.doi.org/10.1016/j.tetasy.2012.10.015 |
| Appears in Collections: | INV - PCSO - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
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| File | Description | Size | Format | |
|---|---|---|---|---|
 Binap-silver salts as chiral-catalysts for the enantioselective.pdf | Versión final (acceso restringido) | 1,3 MB | Adobe PDF | Open Request a copy |
 fullarticleSbF6.pdf | Versión revisada (acceso abierto) | 419,73 kB | Adobe PDF | Open Preview |
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