ChemInform Abstract: Facile Synthesis of Chiral Spirooxindole‐Based Isotetronic Acids and 5‐1H‐Pyrrol‐2‐ones Through Cascade Reactions with Bifunctional Organocatalysts.

Abstract

Unprecedented organocatalyzed asymmetric cascade reactions have been developed for the facile synthesis of chiral spirooxindole-based isotetronic acids and 5-1h-pyrrol-2-ones. the asymmetric 1,2-addition reactions of alpha-ketoesters to isatins and imines by using an acid-base bifunctional 6'-oh cinchona alkaloid catalyst, followed by cyclization and enolization of the resulting adducts, gave chiral spiroisotetronic acids and 5-1h-pyrrol-2-ones, respectively, in excellent optical purities (up to 98% ee). ft-ir analysis supported the existence of hydrogen-bonding interaction between the 6'-oh group of the cinchona catalyst and an isatin carbonyl group, an interaction that might be crucial for catalyst activity and stereocontrol.