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Abstract:

A mild and efficient procedure for the aza-Michael addition of amines to acrylates by using lipases as catalysts is reported. Various lipases, mono- and bifunctional amines, alkyl acrylates, and reaction parameters were studied. Under the optimal conditions, Rhizomucor miehei lipase showed high selectivity. It catalyzed the formation of the Michael monoadduct 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 the 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 22 N-substituted β-amino esters, 15 of them being new products. A mild and efficient enzymatic method for the aza-Michael addition of mono- and bifunctional amines to acrylates was developed. The high substrate specificity showed by Rhizomucor miehei lipase as the catalyst for this reaction was a key feature for obtaining various N-substituted β-amino esters in high yield and purity. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Registro:

Documento: Artículo
Título:Promiscuous behavior of Rhizomucor miehei lipase in the synthesis of N-substituted β-amino esters
Autor:Monsalve, L.N.; Gillanders, F.; Baldessari, A.
Filiación:Departamento de Química Orgánica y UMYMFOR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellõn 2, Piso 3. C1428EGA, Buenos Aires, Argentina
Palabras clave:Amino esters; Enzyme catalysis; Michael addition
Año:2012
Número:6
Página de inicio:1164
Página de fin:1170
DOI: http://dx.doi.org/10.1002/ejoc.201101624
Título revista:European Journal of Organic Chemistry
Título revista abreviado:Eur. J. Org. Chem.
ISSN:1434193X
CODEN:EJOCF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n6_p1164_Monsalve

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Citas:

---------- APA ----------
Monsalve, L.N., Gillanders, F. & Baldessari, A. (2012) . Promiscuous behavior of Rhizomucor miehei lipase in the synthesis of N-substituted β-amino esters. European Journal of Organic Chemistry(6), 1164-1170.
http://dx.doi.org/10.1002/ejoc.201101624
---------- CHICAGO ----------
Monsalve, L.N., Gillanders, F., Baldessari, A. "Promiscuous behavior of Rhizomucor miehei lipase in the synthesis of N-substituted β-amino esters" . European Journal of Organic Chemistry, no. 6 (2012) : 1164-1170.
http://dx.doi.org/10.1002/ejoc.201101624
---------- MLA ----------
Monsalve, L.N., Gillanders, F., Baldessari, A. "Promiscuous behavior of Rhizomucor miehei lipase in the synthesis of N-substituted β-amino esters" . European Journal of Organic Chemistry, no. 6, 2012, pp. 1164-1170.
http://dx.doi.org/10.1002/ejoc.201101624
---------- VANCOUVER ----------
Monsalve, L.N., Gillanders, F., Baldessari, A. Promiscuous behavior of Rhizomucor miehei lipase in the synthesis of N-substituted β-amino esters. Eur. J. Org. Chem. 2012(6):1164-1170.
http://dx.doi.org/10.1002/ejoc.201101624