Highly efficient diastereo- and enantioselective Michael addition reactions between 3-substituted oxindoles and trifluoromethylated nitro olefins catalyzed by a quinine-derived squaramide have been investigated. The corresponding adducts, each bearing a chiral tertiary carbon center attached to a trifluoromethyl group and adjacent to a quaternary stereocenter at the C3 position of the oxindole, were obtained in good to excellent yields (up to 99 %) and with high diastereoselectivities (up to >20:1 dr) and excellent enantioselectivities (up to 99 % ee).

An efficient diastereo- and enantioselective [3+2] cycloaddition reaction of α-aryl isocyanoacetates to isatins catalyzed by a quinine-derived bifunctional amine-thiourea-bearing sulfonamide as multiple hydrogen-bonding donor catalyst has been investigated. The corresponding adducts, which bear a spirocyclic quaternary stereocenter at the C-3 position of the oxindole, were obtained in good yields (51–95%), high diastereoselectivities (up to >20:1 dr) and good to excellent enantioselectivities (up to 97% ee).

An efficient enantioselective allylic amination of Morita–Baylis–Hillman (MBH) carbonates derived from methyl acrylate and aromatic aldehydes with isatins has been realized in the presence of commercially available cinchona alkaloids. The allylic amination products were obtained in moderate-to-good yields (46–74 %) with moderate-to-good enantioselectivities (up to 89 % ee) under mild conditions. The synthetic utility of the amination products has been well demonstrated by the facile synthesis of methyl (3R,4R)-10-oxo-4-phenyl-2,3,4,10-tetrahydropyrimido[1,2-a]indole-3-carboxylate.

A highly enantioselective Michael addition of 3-aryloxindole to phenyl vinyl sulfone catalyzed by a quinine-derived bifunctional amine–thiourea-bearing sulfonamide as multiple hydrogen-bonding donor catalyst has been investigated. The corresponding adducts, which contain a chiral quaternary carbon center at the 3-position of the oxindole, were obtained in moderate-to-good yields (52–86 %) with high-to-excellent enantioselectivities (83–98 % ee).