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 Química orgánica
K1 N-Boc ketimines
K1 Bifunctional squaramide catalyst
K1 Organocatalytic asymmetric synthesis
K1 Cetiminas N-Boc
K1 Catalizador de escuaramida bifuncional
K1 Síntesis asimétrica organocatalítica
K1 2306 Química Orgánica
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/10324/60150
UL https://uvadoc.uva.es/handle/10324/60150
LA eng
NO Organic & Biomolecular Chemistry, 2023, Vol. 21, Issue 11, pp. 2361-2369
NO Producción Científica
DS UVaDOC
RD 14-oct-2024