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Título
Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
Autor
Año del Documento
2022
Editorial
MDPI
Descripción
Producción Científica
Documento Fuente
Molecules, 2022, vol. 27, n. 20, 6983
Abstract
A series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in enantioselective Mannich reactions with different 1,3-dicarbonyl compounds. This method provides a direct pathway to access the 4-amino-5-pyrazolone derivatives bearing a quaternary substituted stereocenter and containing two privileged structure motifs, the β-diketone and pyrazolinone substructures. The adducts were obtained in excellent yields (up to 90%) and enantioselectivities (up to 94:6 er) by employing a very low loading of 2 mol% of a quinine-derived bifunctional squaramide as an organocatalyst for a wide range of substrates. In addition, the utility of the obtained products was demonstrated through one step transformations to enantioenriched diheterocyclic systems (4-pyrazolyl-pyrazolone and 4-isoxazolyl-pyrazolone), potentially promising candidates for drug discovery.
Palabras Clave
Organocatalysis
Organocatálisis
Ketimines
Cetiminas
Pyrazolone
Pirazolona
ISSN
1420-3049
Revisión por pares
SI
Version del Editor
Propietario de los Derechos
© 2022 The Authors
Idioma
eng
Tipo de versión
info:eu-repo/semantics/publishedVersion
Derechos
openAccess
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