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.
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