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Título
Access to Spiropyrazolone-butenolides through NHC-Catalyzed [3 + 2]-Asymmetric Annulation of 3-Bromoenals and 1H-Pyrazol-4,5-diones
Año del Documento
2023
Editorial
American Chemical Society
Descripción
Producción Científica
Documento Fuente
The Journal of Organic Chemistry, 2023, vol. 88, n. 11, pp. 6890–6900
Résumé
The stereoselective synthesis of spirocyclic pyrazo-
lin-5-ones by N-heterocyclic carbene (NHC) organocatalysis has
been less studied so far. For this reason and considering the interest
of 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. The
spirobutenolides have been obtained in good yields (up to 88%)
and enantioselectivities (up to 97:3 er). This constitutes the first
described example using pyrazoldiones as the starting materials for
this class of spiro compounds.
Materias (normalizadas)
Química
Química orgánica
Materias Unesco
23 Química
Palabras Clave
Organocatalysis
Spirobutenolides
Enantioselectivities
Organocatálisis
Espirobutenólidos
Enantioselectividades
ISSN
0022-3263
Revisión por pares
SI
Patrocinador
Junta de Castilla y León predoctoral fellowship (EDU/556/2019)
Version del Editor
Propietario de los Derechos
© 2023 The Authors
Idioma
eng
Tipo de versión
info:eu-repo/semantics/publishedVersion
Derechos
openAccess
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