Abstract
The Pummerer-type reaction of acyclic and rigid cyclic sulfoxides with ketene tert-butyldimethylsilyl methyl acetal 2 in the presence of a catalytic amount of zinc iodide in acetonitrile has been shown to proceed with highly stereoselective deprotonation of the α-methylene proton. A plausible reaction mechanism involving an anti elimination process is proposed based on an isotope labelling experiment using syn- and anti-[α-2H1]benzyl methyl and [α-2H1]benzyl tert-butyl sulfoxides.
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