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Organocatalytic Enantioselective Aminoalkylation Of Pyrazol-3-ones With Aldimines Generated In Situ From α-amido Sulfones.

Laura Carceller-Ferrer, Carlos Vila, G. Blay, I. Fernández, M. C. Muñoz, J. Pedro
Published 2019 · Chemistry, Medicine

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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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