An Easy Entry to Optically Active Spiroindolinones: Chiral Brønsted Acid-Catalysed Pictet-Spengler Reactions of Isatins

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‐tetrahy...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2011-04, Vol.353 (6), p.860-864
Main Authors: Duce, Sara, Pesciaioli, Fabio, Gramigna, Lucia, Bernardi, Luca, Mazzanti, Andrea, Ricci, Alfredo, Bartoli, Giuseppe, Bencivenni, Giorgio
Format: Article
Language:English
Subjects:
asymmetric catalysis
Asymmetry
Bearing
Brønsted acids
Catalysis
Catalysts
Catalysts: preparations and properties
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Noncondensed benzenic compounds
Optical activity
Organic chemistry
organocatalysis
Phosphoric acid
Pictet-Spengler reaction
Preparations and properties
spirooxindoles
Synthesis
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Transformations
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Summary: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.
ISSN:1615-4150
1615-4169
1615-4169
DOI:10.1002/adsc.201100050