Enantioselective 1,3-dipolar cycloadditions of azlactones and electrophilic alkenes catalyzed by dimeric BinapAuTFA complexes
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http://hdl.handle.net/10045/20247
| Title: | Enantioselective 1,3-dipolar cycloadditions of azlactones and electrophilic alkenes catalyzed by dimeric BinapAuTFA complexes |
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| Authors: | Martín Rodríguez, María | Nájera, Carmen | Sansano, Jose M. |
| Research Group/s: | Procesos Catalíticos en Síntesis Orgánica |
| Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica |
| Keywords: | Gold | Binap | Cycloaddition | Azomethine ylides | Asymmetric catalysis |
| Knowledge Area: | Química Orgánica |
| Date Created: | 2011 |
| Issue Date: | 2011 |
| Publisher: | Georg Thieme Verlag |
| Citation: | MARTÍN RODRÍGUEZ, María; NÁJERA, Carmen; SANSANO, José M. "Enantioselective 1,3-dipolar cycloadditions of azlactones and electrophilic alkenes catalyzed by dimeric BinapAuTFA complexes". Synlett, 2012, 23. ISSN 0936-5214, pp. 62-65 |
| Abstract: | Glycine-derived azlactones react with maleimides using (S)- or (R)-dimeric BinapAuTFA complexes affording the corresponding cycloadducts in good yields and high enantioselections (up to 99% ee). The intermediate carboxylic acids are treated with trimethylsilyldiazomethane and isolated as Δ¹-pyrroline methyl esters. These cycloadducts are transformed into exo-proline derivatives by reduction with NaBH3CN in acidic media. On the other hand, N-benzoylalanine-derived oxazolone reacts with tert-butyl acrylate providing the cycloadduct with the ester group at the 3-position with a trans-relative configuration with respect to the methyl ester group. |
| Sponsor: | This work has been supported by the Spanish Ministerio de Ciencia e Innovación (MICINN) [Consolider INGENIO 2010 CSD2007-00006, CTQ2007-62771/BQU, CTQ2010-20387, FEDER, Generalitat Valenciana (PROMETEO/2009/039)], and by the University of Alicante. M.M.-R. also thanks MICINN for a grant. |
| URI: | http://hdl.handle.net/10045/20247 |
| ISSN: | 0936-5214 (Print) | 1437-2096 (Online) |
| DOI: | 10.1055/s-0030-1260334 |
| Language: | eng |
| Type: | info:eu-repo/semantics/article |
| Rights: | © Georg Thieme Verlag Stuttgart New York. http://www.thieme-connect.com/ejournals/toc/synlett |
| Peer Review: | si |
| Publisher version: | http://dx.doi.org/10.1055/s-0030-1260334 |
| Appears in Collections: | INV - PCSO - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
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