Organocatalytic Enantioselective Synthesis of Chiral Spiro-indoline-pyrazolones through a formal [4+1] Annulation Reaction of 4-Bromopyrazolones and aza-ortho-Quinone Methides

Carceller-Ferrer, Laura; Rodríguez Arias, Carlos; Montesinos Magraner, Marc; Sanz Marco, Amparo; Hostalet Romero, Judit; Blay Llinares, Gonzalo; Pedro, José Ramón; Vila Descals, Carlos

Organocatalytic Enantioselective Synthesis of Chiral Spiro-indoline-pyrazolones through a formal [4+1] Annulation Reaction of 4-Bromopyrazolones and aza-ortho-Quinone Methides

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Identifiers

URI: https://hdl.handle.net/10550/96904

DOI: 10.1002/hlca.202400029

Publication date

2024

Authors

Carceller-Ferrer, Laura

Rodríguez Arias, Carlos

Montesinos Magraner, Marc

Sanz Marco, Amparo

Hostalet Romero, Judit

Blay Llinares, Gonzalo

Pedro, José Ramón

Vila Descals, Carlos

Publisher

Wiley

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Abstract

In this communication, a straighforward asymmetric synthesis of spiro-indoline-pyrazolone compounds is described. This methodology consists in a formal [4+1] cycloaddition reaction of 4-bromopyrazolones and aza-ortho-quinone methides generated in situ catalyzed by a bisquinine-derived squaramide in CHCl3 under basic conditions. A variety of chiral spirocyclic compounds bearing a pyrazolone and an indoline moieties were obtained in moderate to good yields (up to 68 %) and moderate to excellent enantioselectivities (up to 93 % ee).

Keywords

química

Bibliographic reference

Carceller‐Ferrer, L., Rodríguez‐Arias, C., Montesinos‐Magraner, M., Sanz‐Marco, A., Hostalet‐Romero, J., Blay, G., Pedro, J. R., & Vila, C. (2024). Organocatalytic Enantioselective Synthesis of Chiral Spiro‐indoline‐pyrazolones through a formal [4+1] Annulation Reaction of 4‐Bromopyrazolones and aza‐ortho‐Quinone Methides. En Helvetica Chimica Acta. Wiley. https://doi.org/10.1002/hlca.202400029

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