Iron(II)-promoted amidoglycosylation and amidochlorination of an allal C3–azidoformate

Iron(II) halides promoted intramolecular alkene amidation in a C3–allal azidoformate. In the presence of alcohols, one-pot β-glycosylation followed. Without added alcohol, amidochlorination occurred using FeCl2, providing an anomeric mixture of glycosyl chlorides which could be used in subsequent silver ion-mediated couplings. A 2-amido glycosyl chloride with a nitrogen-bound iron center is proposed as the glycosylating agent for the in situ amidoglycosylations with FeCl2.