HIGHLY DIASTEREOSELECTIVE OZONE-MEDIATED OXIDATIONS OF 2 6-MEMBERED RING VINYL SULFIDES APPENDED WITH A SPATIALLY PROXIMATE HYDROXYL GROUP

Ozone adds in high yield and stereoselectively to isomerically pure cy clohexenyl methyl sulfides 4a and 4b having a neighboring hydroxyl gro up as a result of conformational and stereoelectronic factors. Further diasteroselective self-induced oxidation of beta'-hydroxy alpha,beta- epoxysulfides intermediates to the corresponding sulfoxides 8a and 8b, respectively, is attributed to incipient hydrogen bonding between the substrate hydroxyl group and the ozone molecule. The configurational and conformational assignments of these hydroxy alpha,beta-epoxysulfox ides are provided by spectroscopic studies.