Synthesis of Chiral Aziridines from Glycals: Application in the Synthesis of a Piperidine–Azepine Fused Derivative

Vicinal chloroamines derived from glycals have been converted into the corresponding chiral aziridines. Although the formation of a tetrahydrofuran derivative is also possible, reaction conditions were developed to give the azirdines exclusively. One of the aziridines is closely related to a compound used in the synthesis of an advanced intermediate en route to Zanamivir, an antiviral agent. Furthermore, one of the aziridines was converted into a piperidine–azepine fused derivative.