The synthesis of α-nitroxy-substituted oxime derivatives has been achieved by an unprecedented metal-assisted addition of a nitrate anion to bis(oxy)enamines, which are readily available from nitronates or nitroalkanes. The method has a broad scope and provides access to α-nitroxy-oximes and their cyclic ethers including nitroxy-substituted isoxazolines and dihydro-1,2-oxazines, which are of interest as potential NO-donors and intermediates in the synthesis of bioactive molecules.
The method offers access to various cyclic and acyclic α‐nitroxy‐oxime derivatives which are obtained starting from bis(oxy)enamines which may be prepared in situ.
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