Enantioselective construction of 3-hydroxy oxindoles via decarboxylative addition of β-ketoacids to isatins

Abstract

The first highly enantioselective decarboxylative addition of β-ketoacids to isatins mediated by a bifunctional tertiary amine-thiourea catalyst has been developed, allowing facile synthesis of biologically important 3-hydroxy oxindoles in good yields and excellent enantioselectivities. The method reported represents a valuable approach of utilizing β-ketoacids as synthetic equivalents of aryl/alkyl methyl ketone enolates. © 2012 American Chemical Society.