Chiral Urea-Catalyzed Asymmetric Mannich Reaction of 3-Fluoro-oxindoles with α-Amidosulfones: Synthesis of Optically Active α-Fluoro-β-amino-oxindoles

The asymmetric Mannich reaction of 3-fluorooxindoles and alpha-amidosulfones catalyzed by a chiral urea catalyst derived from quinine in presence of K3PO4 was developed. Through the asymmetric reaction, a series of alpha-fluoro-beta-amino-oxindoles, containing a tertiary carbon stereocenter, could be obtained in high yields (up to 95%) with high enantioselectivity (95%) and diastereoselectivity (>99:1). Such alpha-fluoro-beta-amino-oxindole compounds are expected to become candidates in the field of medicine.

Automated summary

In this study, a chiral urea catalyst derived from quinine was used to catalyze the asymmetric Mannich reaction of 3-fluorooxindoles and alpha-amidosulfones. The reaction yielded alpha-fluoro-beta-amino-oxindoles with a tertiary carbon stereocenter in high yields (up to 95%) and exhibited high enantioselectivity (95%) and diastereoselectivity (>99:1). These alpha-fluoro-beta-amino-oxindole compounds are potential candidates in the field of medicine.