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An Easy Entry to Optically Active Spiroindolinones: Chiral Brønsted Acid‐Catalysed Pictet–Spengler Reactions of Isatins
157
Citations
55
References
2011
Year
Bioorganic ChemistryEngineeringOrganic ChemistryChemistryDiversity Oriented SynthesisStereoselective SynthesisPictet–spengler ReactionsBinol‐derived Phosphoric AcidsBiochemistryDiversity-oriented SynthesisEasy EntryOptically Active SpiroindolinonesPharmacologyAsymmetric CatalysisEnantioselective SynthesisBiomolecular EngineeringNatural SciencesAnti‐malarial AgentsSpirooxindole StructuresSynthetic Chemistry
Abstract The first catalytic asymmetric Pictet–Spengler reaction of isatins is presented. BINOL‐derived phosphoric acids were found to be competent catalysts for this transformation, giving challenging spirooxindole structures bearing a quaternary stereocentre with generally good results. The 1,2,3,4‐tetrahydro‐β‐carboline products (spiroindolinones) are the core of some newly discovered anti‐malarial agents.
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