Directed Dihydroxylation of Cyclic Allylic Alcohols and Trichloroacetamides Using OsO₄/TMEDA

Abstract

The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OsO4 is presented and a plausible mechanism described.