Jump to main content
Jump to site search

Issue 7, 1995
Previous Article Next Article

Homochiral 2,3-epoxy sulfides—powerful new synthetic building blocks providing stereoselective access to 2,3-epoxy sulfoxides, 2,3-dihydroxy sulfoxides and (E)-γ-hydroxy-α,β-unsaturated sulfoxides and sulfones. X-Ray molecular structure of rac-(2R*,3R*)-1-[(S*)-phenylsulfinyl] hexane-2,3-diol

Abstract

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 a cyclic sulfite. The synthesis of (E)-γ-hydroxy-α,β-unsaturated sulfones by base-catalysed elimination of a 2,3-epoxy sulfone is also described.

Back to tab navigation

Article type: Paper
DOI: 10.1039/P19950000847
J. Chem. Soc., Perkin Trans. 1, 1995, 847-859

  •   Request permissions

    Homochiral 2,3-epoxy sulfides—powerful new synthetic building blocks providing stereoselective access to 2,3-epoxy sulfoxides, 2,3-dihydroxy sulfoxides and (E)-γ-hydroxy-α,β-unsaturated sulfoxides and sulfones. X-Ray molecular structure of rac-(2R*,3R*)-1-[(S*)-phenylsulfinyl] hexane-2,3-diol

    A. D. Westwell, M. Thornton-Pett and C. M. Rayner, J. Chem. Soc., Perkin Trans. 1, 1995, 847
    DOI: 10.1039/P19950000847

Search articles by author

Spotlight

Advertisements