Vicinal All-Carbon Quaternary Stereocenter Construction with Trifluoromethyl Groups via Organocatalytic Asymmetric Cascade Michael/Michael Reaction

A thiourea organocatalyst efficiently promoted the asymmetric cascade Michael/Michael reactions between isatin-derived trifluoromethylacrylate and alpha-alkylidene succinimide, resulting in high yields of spirooxindole derivatives. These compounds exhibit vicinal all-carbon quaternary stereocenters and bear a trifluoromethyl group, with excellent enantioselectivities reaching up to 99 % ee. This work represents the first successful organocatalyst application for the direct construction of vicinal all-carbon quaternary stereocenters, featuring a trifluoromethyl group.