The enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to isatin-derived ketiminesElectronic supplementary information (ESI) available: Experimental procedure and spectral data for all prepared compounds with copies of the 1H NMR, 13C NMR and 19F NMR and HPLC chromatographs. CCDC 1575684. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7ob02408h

An asymmetric organocatalytic addition of fluorinated phenylsulfonylnitromethane to isatin-derived ketimines was developed. The reaction was efficiently catalyzed by a chiral tertiary amine, cinchonine. This methodology provides a new type of optically active compound with two adjacent quaternary carbon stereocenters in good yield (up to 96%), with moderate diastereoselectivity (up to 5.7 : 1 dr) and excellent enantioselectivity (up to 98/96% ee). Enantioselective fluoroalkylation of isatin-derived ketimines can be effectively catalyzed with cinchona alkaloids affording fluoro-containing compounds bearing adjacent quaternary stereogenic centers.