Abstract
The asymmetric oxidation ( t -BuO 2H, 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, (93% optical yield), is described.
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