Journal of the Chemical Society. Perkin transactions I p. 847 - 860 (1995)
Update date:2022-08-16
Topics:
Westwell, Andrew D.
Thornton-Pett, Mark
Rayner, Christopher M.
The stereoselective transformation of homochiral 2,3-epoxy sulfoxides into 2,3-epoxy sulfoxides is described.These intermediates undergo elimination under basic reaction conditions to give (E)-γ-hydroxy-α,β-unsaturated sulfoxides, and under Lewis acidic conditions form novel cyclic sulfoxonium salts which on hydrolysis give 2,3-dihydroxy sulfoxides with excellent stereochemical control. 2,3-Dihydroxy sulfoxides can also be converted into (E)-γ-hydroxy-α,β-unsaturated sulfoxides by elimination via cyclic sulfide.The synthesis of (E)-γ-hydroxy-α,β-unsaturated sulfones by base-catalysed elimination of a 2,3-epoxy sulfone is also described.
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