Abstract

Abstract Prolinamide (2 S ,4 R )-4-hydroxy- N -(( S )-1-phenylethyl)pyrrolidine-2-carboxamide was found to be an efficient organocatalyst (10 mol %) for the direct asymmetric aldol reactions of isatins with acetone at −35 °C in THF and afforded the product in 79% yield with 74% ee . We have generalised the methodology for the direct asymmetric aldol reaction between isatin derivatives and acetone, and the corresponding aldol products were obtained in high yields (up to 99%) and with moderate enantioselectivities (up to 80%). This method has been applied to the enantioselective synthesis of ( S )-convolutamydine.

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