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Title: Organocatalytic asymmetric Friedel-Crafts reaction of sesamol with isatins: access to biologically relevant 3-aryl-3-hydroxy-2-oxindoles. Author: Kumar A, Kaur J, Chauhan P, Chimni SS. Journal: Chem Asian J; 2014 May; 9(5):1305-10. PubMed ID: 24591414. Abstract: The Friedel-Crafts reaction of electron-rich phenols with isatins was developed by employing bifunctional thiourea-tertiary amine organocatalysts. Cinchona alkaloid derived thiourea epiCDT-3 a efficiently catalyzed the Friedel-Crafts-type addition of phenols to isatin derivatives to provide 3-aryl-3-hydroxy-2-oxindoles 7 and 9 in good yield (80-95 %) with good enantiomeric excess (83-94 %). Friedel-Crafts adduct 7 t was subjected to a copper(I)-catalyzed azide-alkyne cycloaddition to obtain biologically important 3-aryl-3-hydroxy-2-oxindole 11 in good enantiomeric excess and having a 1,2,3-triazole moiety.[Abstract] [Full Text] [Related] [New Search]