UMYMFOR 05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
artículos
Título:
Promiscuous behavior of the Rhizomucor miehei lipase in N-substituted-β-amino esters synthesis
Autor/es:
MONSALVE, L. N.; GILLANDERS, F.; BALDESSARI, A.
Revista:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Editorial:
WILEY-V C H VERLAG GMBH
Referencias:
Año: 2011
ISSN:
1434-193X
Resumen:
A mild and efficient procedure for the aza-Michael addition of amines to acrylates, using lipases as catalysts, is reported. Various lipases, mono- and bifunctional amines, alkyl acrylates and reaction parameters were studied. Under optimal conditions Rhizomucor miehei lipase (LIP) showed high selectivity. It catalyzed the formation of the Michael mono-adduct as the only product in high yield and purity. Moreover, when diamines were used as nucleophiles, the lipase catalyzed the addition of only one of two amino groups, showing in this case high substrate specificity. This promiscuous and highly selective behavior displayed by Rhizomucor miehei lipase allowed us to obtain twenty two N-substituted-β-amino esters, fifteen of them being novel products.
