RT info:eu-repo/semantics/article
T1 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
A1 Gil Ordóñez, Marta
A1 Aubry, Camille
A1 Niño, Cristopher
A1 Maestro Fernández, Alicia
A1 Andrés García, José María
K1 Organocatalysis
K1 Organocatálisis
K1 Ketimines
K1 Cetiminas
K1 Pyrazolone
K1 Pirazolona
AB 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.
PB MDPI
SN 1420-3049
YR 2022
FD 2022
LK https://uvadoc.uva.es/handle/10324/56004
UL https://uvadoc.uva.es/handle/10324/56004
LA eng
NO Molecules, 2022, vol. 27, n. 20, 6983
NO Producción Científica
DS UVaDOC
RD 25-nov-2024