Organocatalytic enantioselective aminoalkylation of pyrazol-3-ones with aldimines generated: In situ from α-amido sulfones

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Abstract

Herein, an efficient asymmetric aminoalkylation of pyrazolones with α-amido sulfones catalyzed by a quinine-derived squaramide in dichloromethane/aqueous media has been established. A variety of chiral amines were obtained with high yields (up to 98%) and excellent enantioselectivities (up to 99% ee). The corresponding products are transformed into optically active acetylated pyrazoles after treatment with Ac2O/Et3N, because of the instability of some adducts. The reaction tolerates a wide range of α-amido sulfones and different pyrazolones.

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Carceller-Ferrer, L., Vila, C., Blay, G., Fernández, I., Muñoz, M. C., & Pedro, J. R. (2019). Organocatalytic enantioselective aminoalkylation of pyrazol-3-ones with aldimines generated: In situ from α-amido sulfones. Organic and Biomolecular Chemistry, 17(46), 9859–9863. https://doi.org/10.1039/c9ob02252j

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