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

Autor: Carceller‐Ferrer, Laura, Rodríguez‐Arias, Carlos, Montesinos‐Magraner, Marc, Sanz‐Marco, Amparo, Hostalet‐Romero, Judit, Blay, Gonzalo, Pedro, José R., Vila, Carlos
Zdroj: Helvetica Chimica Acta; Apr2024, Vol. 107 Issue 4, p1-8, 8p
Abstrakt: 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). [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index