Enantioselective Nitroso Aldol Intramolecular Transesterification Cyclization Domino Reaction for Highly Effective Construction of Chiral Spirooxindoles

A catalytic asymmetric nitroso aldol intramolecular transesterification cyclization domino reaction between a C3 alkyl ester substituted oxindole and nitrosobenzene for the construction of chiral spirooxindoles was achieved in the presence of a chiral bifunctional tertiary amine thiourea catalyst and water. Optically active spirooxindoles were obtained in moderate yields (up to 76 %) and excellent enantioselectivities (up to 95 % ee ).