Regio- and stereo-selective synthesis of aryL 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides

摘要

The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount of'Pd(OAc)_2 to form pyranoid aryl C-glycosides has been achieved. The reaction takes p1ace smoothly in the presence of Ag_2CO_3 and Cu(OAc)_2 (or DMSO) in acetonitrile. This ary1ation process, which occurs in a highly regio- and stereo-selective manner, provides a simple, mild, and efficient approach to the synthesis of aryl 2-deoxy-C-glycopyranosides.