THE DIRECTED DIHYDROXYLATION OF ALLYLIC ALCOHOLS

The preparation and dihydroxylation of a series of polyenes and cyclic allylic alcohols using the TMEDA/osmium tetroxide mixture is reported , Remarkably, these reagents lead to high levels of regiochemical and stereochemical control as the oxidant hydrogen-bonds to the allylic al cohol group, A mechanistic hypothesis is presented which invokes the f ormation of a reactive, bidentate complex between osmium tetroxide and TMEDA at low temperatures. (C) 1997 Elsevier Science Ltd.