AN EFFICIENT SYNTHESIS OF BOTH ENANTIOMERS OF CHIRAL NON RACEMIC METHYLSULFOXIDES FROM DAG

Article abstract of DOI:10.1016/0040-4039(91)80503-X

Diacetone-D-Glucose is stereoselectively converted to its (S)- or (R)-methanesulfinates 1 and 2 in 90 and 87 percent yield by treatment with methylsulfinyl chloride in the presence of diisopropylethylamine or pyridine, respectively.After purification, sulfinates 1 and 2 were transformed into both epimers of enantiomerically pure methylsulfoxides by reaction with Grignard reagents.