RESUMEN
The atroposelective electrophilic sulfenylation of biaryl anilines has been realized for the first time. The reaction is enabled by a new chiral 6,6'-dianisole substituted SPINOL-derived selenide. A variety of axially chiral sulfur-containing biaryl aniline compounds were obtained in moderate to excellent yields with moderate to excellent enantioselectivities. The experimental results suggest that catalyst rigidity is important for the high atroposelectivity.
RESUMEN
An enantioselective selenocyclization of 1,1-disubstituted alkenes was achieved for the first time, which is enabled by a novel combination of a chiral BINAM-derived sulfide and an achiral Lewis acid. Various selenium-containing 4H-3,1-benzoxazines, which are widely present in a range of medicinally relevant molecules, were readily obtained in moderate to good yields and good to excellent enantioselectivities. A series of tetrasubstituted carbon stereocenters were facilely constructed.