6533b857fe1ef96bd12b4f4a
RESEARCH PRODUCT
Organocatalytic enantioselective aminoalkylation of pyrazol-3-ones with aldimines generated in situ from α-amido sulfones
Isabel FernándezCarlos VilaLaura Carceller-ferrerGonzalo BlayM. Carmen MuñozJosé R. Pedrosubject
In situchemistry.chemical_classificationAldimine010405 organic chemistryOrganic ChemistryEnantioselective synthesisSquaramide010402 general chemistry01 natural sciencesBiochemistry0104 chemical sciencesAdductCatalysischemistry.chemical_compoundCatàlisichemistryPyrazolonesOrganic chemistryPhysical and Theoretical ChemistryQuímica orgànicaDichloromethanedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-11-14 | Organic & Biomolecular Chemistry |