6533b822fe1ef96bd127d649

RESEARCH PRODUCT

Catalytic Diastereo- and enantioselective vinylogous Mannich reaction of alkylidenepyrazolones to isatin-derived ketimines

Gonzalo BlayCarlos VilaJosé R. PedroM. Carmen MuñozLaura Carceller-ferrer

subject

LetterChemistryIsatinOrganic ChemistrySquaramideEnantioselective synthesisBiochemistryCatalysisAdductReaccions químiqueschemistry.chemical_compoundCatàlisiYield (chemistry)Organic chemistryPhysical and Theoretical ChemistryMannich reactionQuímica orgànica

description

A valuable organocatalytic vinylogous Mannich reaction between alkylidenepyrazolones and isatin-derived ketimines has been successfully established. Squaramide organocatalyst, prepared from quinine, catalyzed the diastereo- and enantioselective vinylogous Mannich addition, affording a range of aminooxindole-pyrazolone adducts (24 examples) with excellent outcomes: up to 98% yield with complete diastereoselectivity and excellent enantioselectivity (up to 99% ee). Additionally, different synthetic transformations were performed with the chiral pyrazolone-oxindole adducts.

yearjournalcountryeditionlanguage
2021-01-01
10.1021/acs.orglett.1c02571https://hdl.handle.net/10550/80411