Artículo
Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
Gandolfi Donadío, Lucía
; Galetti, Mariana Alejandra; Giorgi, Gianluca; Rasparini, Marcello; Comin, Maria Julieta
Fecha de publicación:
09/2016
Editorial:
American Chemical Society
Revista:
Journal of Organic Chemistry
ISSN:
0022-3263
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
Using the reaction between phenylacetaldehyde and nitrostyrene catalyzed by pyrrolidine as a simple model, we have studied the diastereochemical outcome of the organocatalytic Michael reactions between benzylic aldehydes and nitrostyrenes. We found that the anti adduct was obtained in high yield and diastereoselection as was demonstrated by the X-ray structure of the product. In situ NMR studies showed a different reaction pathway when compared to aliphatic aldehydes that yield the syn adduct as major isomer.
Palabras clave:
Michael Addition
,
Phenylacetheldehyde
,
Organocatalyst
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Articulos(SEDE CENTRAL)
Articulos de SEDE CENTRAL
Articulos de SEDE CENTRAL
Citación
Gandolfi Donadío, Lucía; Galetti, Mariana Alejandra; Giorgi, Gianluca; Rasparini, Marcello; Comin, Maria Julieta; Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene; American Chemical Society; Journal of Organic Chemistry; 81; 17; 9-2016; 7952-7957
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