A new method for the dehydration of β-hydroxy sulfones: synthesis of (E,S)-γ-hydroxy-α,β-unsaturated sulfones and (S)-ε-hydroxy-(E,E)-α,γ-dienyl sulfones

Abstract

Optically active (E,S)-γ-hydroxy-α,β-unsaturated sulfones and (S)-ε-hydroxy-(E,E)-α,γ-dienyl sulfones have been prepared in a one-pot dehydration procedure from β,γ-dihydroxy sulfones and δ,ε-dihydroxy allyl, sulfones, respectively, via an elimination reaction of the corresponding cyclic sulfites or carbonates formed in situ by treatment with thionyl chloride or carbonyldiimidazole.