Biocatalytic synthesis of chiral N-(2-hydroxyalkyl)-acrylamides

The preparation of a series of novel chiral N-(2-hydroxylalkyl)-acrylamides through a lipase-catalyzed resolution of racemic alkanolamines is described. The absolute stereochemistry and enantiomeric excess of the products were determined by a modified Mosher's method. The method was validated f...

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Detalles Bibliográficos
Autores: Monsalve, Leandro Nicolas, Rustoy, Eduardo Miguel, Baldessari, Alicia
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2011
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/84703
Acceso en línea:http://hdl.handle.net/11336/84703
Access Level:acceso abierto
Palabra clave:CANDIDA ANTARCTICA LIPASE B
MOSHER' S METHOD
N-(HYDROXYALKYL)-ACRYLAMIDES
PRIMARY ALCOHOL
STEREOSELECTIVITY
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descripción
Sumario:The preparation of a series of novel chiral N-(2-hydroxylalkyl)-acrylamides through a lipase-catalyzed resolution of racemic alkanolamines is described. The absolute stereochemistry and enantiomeric excess of the products were determined by a modified Mosher's method. The method was validated for this particular case by the synthesis of an enantiomerically pure product. Moreover, the stereoselective behavior of the lipase in this reaction is discussed.