119577-17-2Relevant academic research and scientific papers
Fungal biotransformation of 1,3-oxathiolanes
Holland, Herbert L.,Munoz, Benito
, p. 2299 - 2303 (2007/10/02)
A series of 2,2-disubstituted 1,3-oxathiolanes has been incubated with fungi known to be capable of efficient asymmetric oxidation of sulfides to sulfoxides.In three cases (2-phenyl-1,3-oxathiolane, 2-methyl-2-phenyl-1,3-oxathiolane, and 2-tert-butyl-2-phenyl-1,3-oxathiolane), sulfoxidation occured to give a single diastereomer of sulfoxide, whose relative stereochemistry has been assigned by 1H nuclear magnetic resonance analysis.The sulfoxides were obtained as racemates or had low enantiomeric enrichment.In some cases ketones, assumed to be formed by spontaneous hydrolysis of oxathiolane sulfoxides, were obtained, together with their reduction products, secondary alcohols.
ASYMMETRIC OXIDATION OF 1,3-DITHIOLANES. A ROUTE TO THE OPTICAL RESOLUTION OF CARBONYL COMPOUNDS
Bortolini, O.,Furia, F. Di,Licini, G.,Modena, G.,Rossi, M.
, p. 6257 - 6260 (2007/10/02)
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.
