An approach to the synthesis of α‐halo oxime ethers from readily accessible nitronates and nitro compounds via bis(oxy)enamines is reported. A key step of the strategy involves the unprecedented reaction of bis(oxy)enamines with a metal (Co, Zn, Mg, Mn) halide that acts as both a promoter and halide (Br, I, Cl) source. A variety of cyclic and acyclic ethers of α‐halo oximes, including previously unavailable trimethylsilyl ethers of α‐iodo oximes, have been synthesized in good‐to‐high yields.

Bis(oxy)enamines (I) and (XII) undergo an unprecedented reaction with cobalt(II) halides to produce a variety of cyclic and acyclic ethers of α‐halo oximes including previously unavailable trimethylsilyl ethers of α‐iodo oximes.