Organocatalytic asymmetric syntheses of 3-fluorooxindoles containing vicinal fluoroamine motifs

Abstract

An organocatalytic Mannich reaction of 3-fluorooxindoles has been developed. Using a commercially available cinchona alkaloid catalyst, a wide range of 3-fluorooxindoles was successfully reacted with N-sulfonyl aldimines to give biologically important 3-fluorooxindoles containing vicinal fluoroamine motifs with high efficiency and good enantioselectivity. This protocol uses readily available reactants and cheap organocatalysts, and it is operationally simple.