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

Abstract

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. (C) 2012 Elsevier Ltd. All rights reserved.