RT info:eu-repo/semantics/article
T1 Organocatalytic asymmetric synthesis of oxazolidino spiropyrazolinones via N,O-acetalization/aza Michael addition domino reaction between N-Boc pyrazolinone ketimines and γ-hydroxyenones
A1 Gil Ordóñez, Marta
A1 Martín Maroto, Laura
A1 Maestro Fernández, Alicia
A1 Andrés García, José María
K1 Organocatalytic asymmetric synthesis
K1 Síntesis organocatalítica
K1 23 Química
AB A squaramide-catalyzed asymmetric N,O-acetalization/aza Michael addition domino reaction between N-Boc ketimines derived from pyrazolin-5-ones and γ-hydroxyenones has been developed for the construction of pyrazolinone embedded spirooxazolidines. A hydroquinine derived bifunctional squaramide catalyst was found to be the most effective for this cascade spiroannulation. This new protocol allows the generation of two stereocenters and the desired products are obtained in good yields with moderate to good diastereoselectivities (up to 3.3 : 1 dr) and high enantioselectivities (up to >99% ee) from a range of substituted N-Boc pyrazolinone ketimines and γ-hydroxyenones. The developed protocol is amenable for a scale-up reaction.
PB Royal Society of Chemistry
SN 1477-0520
YR 2023
FD 2023
LK https://uvadoc.uva.es/handle/10324/58844
UL https://uvadoc.uva.es/handle/10324/58844
LA eng
NO Organic and Biomolecular Chemistry, 2023
NO Producción Científica
DS UVaDOC
RD 25-nov-2024