Microwave-assisted multicomponent diastereoselective 1,3-dipolar cycloaddition of ethyl glyoxylate derived azomethine ylides
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Título: | Microwave-assisted multicomponent diastereoselective 1,3-dipolar cycloaddition of ethyl glyoxylate derived azomethine ylides |
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Autor/es: | Mancebo Aracil, Juan | Nájera, Carmen | Sansano, Jose M. |
Grupo/s de investigación o GITE: | Procesos Catalíticos en Síntesis Orgánica |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Departamento de Química Orgánica |
Palabras clave: | Cycloaddition | Azomethine |
Área/s de conocimiento: | Química Orgánica |
Fecha de creación: | 2012 |
Fecha de publicación: | 6-dic-2012 |
Editor: | Royal Society of Chemistry |
Cita bibliográfica: | MANCEBO-ARACIL, Juan; NÁJERA, Carmen; SANSANO, José M. “Microwave-assisted multicomponent diastereoselective 1,3-dipolar cycloaddition of ethyl glyoxylate derived azomethine ylides”. Organic & Biomolecular Chemistry. Vol. 11, Issue 4 (2013). ISSN 1477-0520, pp. 662-675 |
Resumen: | The thermal multicomponent 1,3-dipolar cycloaddition (1,3-DC) of diethyl aminomalonate or α-amino esters (derived from glycine, alanine, phenylalanine, and phenylglycine) with ethyl glyoxylate and the corresponding dipolarophile such as maleimides, methyl acrylate, methyl fumarate, (E)-1,2-bis(phenylsulfonyl)ethylene, and electron deficient alkynes allows the diastereoselective synthesis of new polysubstituted pyrrolidine derivatives. Microwave-assisted heating processes give better results than conventional heating ones, affording endo-cycloadducts as major stereoisomers. In general, 2,5-cis-cycloadducts are preferentially formed according to the previous formation of the W-shaped dipole. Only in the 1,3-DC of the disulfone with phenylglycine and ethyl glyoxylate the corresponding exo-trans-cycloadduct was isolated. The compound endo-cis-4b, derived from phenylalanine, ethyl glyoxylate and N-benzylmaleimide, has been further transformed into a very complex diazabicyclo[2.2.1]octane skeleton with potential biological activity. |
Patrocinador/es: | This work has been supported by the Spanish Ministerio de Ciencia e Innovación (MICINN) (Consolider INGENIO 2010 CSD2007-00006, CTQ2010-20387), FEDER, Generalitat Valenciana (PROMETEO/2009/039), and by the University of Alicante. |
URI: | http://hdl.handle.net/10045/25778 |
ISSN: | 1477-0520 (Print) | 1477-0539 (Online) |
DOI: | 10.1039/c2ob27072b |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Revisión científica: | si |
Versión del editor: | http://dx.doi.org/10.1039/C2OB27072B |
Aparece en las colecciones: | INV - PCSO - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
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