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

Abstract

Abstract Ozone adds in high yield and stereoselectively to isomerically pure cyclohexenyl methyl sulfides 4a and 4b having a neighboring hydroxyl group as a result of conformational and stereoelectronic factors. Further diasteroselective self-induced oxidation of β'-hydroxy α,β-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 α,β-epoxysulfoxides are provided by spectroscopic studies.