A Route to Polysubstituted Aziridines from Carbenes and Imines through a Nondiazo Approach

An
efficient method for the synthesis of polysubstituted aziridines
utilizing enynones and imines is described. This transformation is
achieved through the reaction of imines with donor/donor carbene intermediates,
which were generated in situ from the cyclization of enynones. Furthermore,
the resulted aziridines were good 1,3-dipoles, which could be efficiently
trapped by dipolarophiles to give five-membered heterocycles. The
obvious advantages of wide substrate scopes, mild reaction conditions,
and high atom efficiency make this system highly appealing for construction
of polysubstituted aziridines, 2,5-dihydropyroles, and 1,2,4-triazolidines.