ENANTIOSELECTIVE PREPARATION OF 1,3-DITHIANE 1-OXIDES BY ASYMMETRIC OXIDATION OF 1,3-DITHIANES BEARING A CHIRAL AUXILIARY
Citation
Y. Watanabe et al., ENANTIOSELECTIVE PREPARATION OF 1,3-DITHIANE 1-OXIDES BY ASYMMETRIC OXIDATION OF 1,3-DITHIANES BEARING A CHIRAL AUXILIARY, Journal of the Chemical Society. Perkin transactions. I, (15), 1996, pp. 1879-1885
Categorie Soggetti
Chemistry Inorganic & Nuclear
SICI code
0300-922X(1996):15<1879:EPO11B>2.0.ZU;2-K
Abstract
Oxidation of 1,3-dithianes bearing a chiral auxiliary derived from (+)
or (-)-camphor or diacetone D-(+)-glucose by the Sharpless reagent [T
i(OPr1)(4)-diethyl L-(+)- or D-(-)-tartrate-Bu(t)OOH] affords, with hi
gh stereoselectivity, the monosulfoxides in good to excellent yields.
Removal of the chiral auxiliary by base-catalysed hydrolysis yields (R
)- and (S)-1,3-dithiane 1-oxides in high yields.
