HOMOCHIRAL 2,3-EPOXY SULFIDES - POWERFUL NEW SYNTHETIC BUILDING-BLOCKS PROVIDING STEREOSELECTIVE ACCESS TO 2,3-EPOXY SULFOXIDES, 2,3-DIHYDROXY SULFOXIDES AND (E)-GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED SULFOXIDESAND SULFONES - X-RAY MOLECULAR-STRUCTURE OF SK)-1-[(S-ASTERISK)-PHENYLSULFINYL]HEXANE-2,3-DIOL

The stereoselective transformation of homochiral 2,3-epoxy sulfoxides into 2,3-epoxy sulfoxides is described. These intermediates undergo el imination under basic reaction conditions to give (E)-gamma-hydroxy-al pha,beta-unsaturated sulfoxides, and under Lewis acidic conditions for m novel cyclic sulfoxonium salts which on hydrolysis give 2,3-dihydrox y sulfoxides with excellent stereochemical control. 2,3-Dihydroxy sulf oxides can also be converted into (E)-gamma-hydroxy-alpha,beta-unsatur ated sulfoxides by elimination via a cyclic sulfite. The synthesis of (E)-gamma-hydroxy-alpha,beta-unsaturated sulfones by base-catalysed el imination of a 2,3-epoxy sulfone is also described.