ASYMMETRIC OXIDATION OF 1,3-DITHIOLANES. A ROUTE TO THE OPTICAL RESOLUTION OF CARBONYL COMPOUNDS

Article abstract of DOI:10.1016/S0040-4039(00)85446-5

The asymmetric oxidation (t-BuO2H, Ti(OPr-i)4, DET) of a series of 1,3-dithiolanes was carried out to produce the corresponding S-oxides with high chemical and optical yields.By contrast, the oxidation of 1,3-dithianes and 1,3-oxathiolane prepared from the same carbonyl compounds gave much lower optical yields.The optical resolution of the model ketone, dl-menthone, via a) 1,3-dithiolane formation b) asymmetric S-oxidation c) chromatographic diasteromeric separation d) regeneration of the carbonyl group, (93percent optical yield), is described.