Enantioselective Mannich Reactions of 3‑Fluorooxindoles with Cyclic N‑Sulfamidate Aldimines

Both the 3-fluorooxindole and cyclic sulfamidate frameworks are important in medicinal chemistry owing to their associated biological activities. We report an approach accessing 3-fully substituted 3-fluorooxindoles, containing a benzo-fused sulfamidate subunit through highly enantioselective Mannich-type reactions between 3-fluorooxindoles and cyclic benzo-fused N-sulfamidate aldimines. These reactions are promoted by a commercially available cinchona alkaloid catalyst, accommodate a broad substrate scope, and deliver the desired products in a yield of up to 99% with an enantiomeric excess of up to 94%. A plausible reaction pathway is also presented.