Anodic generation of a zirconium catalyst for Ferrier rearrangement and hetero Michael addition

An efficient catalyst for Ferrier rearrangement and hetero-Michael addition was successfully generated from a sacrificial zirconium anode into media containing reactants for these reactions. Thus, the catalyst generated, successfully promoted the allylic rearrangement of peracetylated d-glucal in the presence of a suitable S-nucleophile, giving the corresponding 2,3-unsaturated d-glucopyranose (pseudoglycal) in good to high yields. This catalyst was also shown to be capable of promoting hetero-Michael conjugate addition of S- and N-nucleophiles to the carbon–carbon double bond of methyl vinyl ketone, resulting in new carbon–sulfur and carbon–nitrogen bond formation.