Tetrahedron Letters p. 6257 - 6260 (1986)
Update date:2022-08-04
Topics:
Bortolini, O.
Furia, F. Di
Licini, G.
Modena, G.
Rossi, M.
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.
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