RT info:eu-repo/semantics/article
T1 Access to Spiropyrazolone-butenolides through NHC-Catalyzed [3 + 2]-Asymmetric Annulation of 3-Bromoenals and 1H-Pyrazol-4,5-diones
A1 Gil Ordóñez, Marta
A1 Maestro Fernández, Alicia
A1 Andrés García, José María
K1 Química
K1 Química orgánica
K1 Organocatalysis
K1 Spirobutenolides
K1 Enantioselectivities
K1 Organocatálisis
K1 Espirobutenólidos
K1 Enantioselectividades
K1 23 Química
AB The stereoselective synthesis of spirocyclic pyrazo-lin-5-ones by N-heterocyclic carbene (NHC) organocatalysis hasbeen less studied so far. For this reason and considering the interestof this class of compounds, here, we present the NHC-catalyzed [3+ 2]-asymmetric annulation of β-bromoenals and 1H-pyrazol-4,5-diones that achieves to produce chiral spiropyrazolone-butenolides.The synthesis is general for aryl and heteroaryl β-bromo-α,β-unsaturated aldehydes and 1,3-disubstituted pyrazolones. Thespirobutenolides have been obtained in good yields (up to 88%)and enantioselectivities (up to 97:3 er). This constitutes the firstdescribed example using pyrazoldiones as the starting materials forthis class of spiro compounds.
PB American Chemical Society
SN 0022-3263
YR 2023
FD 2023
LK https://uvadoc.uva.es/handle/10324/59682
UL https://uvadoc.uva.es/handle/10324/59682
LA eng
NO The Journal of Organic Chemistry, 2023, vol. 88, n. 11, pp. 6890–6900
NO Producción Científica
DS UVaDOC
RD 13-may-2024