Unravelling a New Class of Chiral Organocatalyst for Asymmetric Ring-Opening Reaction of Meso Epoxides with Anilines

Chiral sulfinamide based organocatalyst 11 was synthesized from readily available starting materials and used for the asymmetric ring-opening (ARO) reaction of meso epoxides with anilines. A high yield (up to 95%) of chiral β-amino alcohols with excellent enantioselectivity (ee up to 99%) was achieved in 24–30 h at rt under optimized reaction conditions. A probable mechanism for the catalytic ARO reaction is envisaged by 1H and 13C NMR experiments.