Enantioselective Construction of Chiral Bispiro[Oxindole-Pyrrolidine-Pyrazolone] Derivatives via Sequential and One-Pot Mannich/Hydroamination Reaction
Michal Urban, Martin Nigríni, Ivana Cı́sařová, Ján Veselý
Abstract
The atom-economic method for the preparation of novel bispirocyclic compounds containing three fused heterocyclic scaffolds privileged in drug discovery was developed by using a chiral amine-squaramide Mannich reaction and Au(I)-catalyzed hydroamination. The developed synthetic strategy performed either stepwise or as a one-pot process allows the formation of chiral bispirocyclic [oxindole-pyrrolidine-pyrazolones] in high yields (up to 75%) with excellent enantioselectivities (up to 99%).
Topics & Concepts
ChemistryPyrrolidineSquaramideHydroaminationOxindolePyrazolonesEnantioselective synthesisMannich reactionPyrazoloneOrganic chemistryCombinatorial chemistryCatalysisOrganocatalysisAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsOxidative Organic Chemistry Reactions