Asymmetric synthesis of alkane- and arenesulfinates of diacetone-D-glucose (DAG): an improved and general route to both enentiometrically pure sulfoxides

The reaction of diacetone-D-glucose (DAG) with sulfinyl chlorides were observed at -78 degrees Celsius using the bases i-Pr2NEt in toluene and Py in THF. The sulfinates were formed in high yields and purification was generally accomplished by column chromatography. The stereochemistry of the final sulfinate esters depends on the base used. Enantiomerically pure sulfoxides were obtained by reaction with several Grignard reagents.