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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.

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

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Publication details

The article was received on 17 Oct 2019, accepted on 02 Nov 2019 and first published on 06 Nov 2019


Article type: Communication
DOI: 10.1039/C9OB02252J
Org. Biomol. Chem., 2019, Advance Article

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

    L. Carceller-Ferrer, C. Vila, G. Blay, I. Fernández, M. C. Muñoz and J. R. Pedro, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB02252J

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