Enhanced stereoselectivity in the catalytic dihydroxylation of acyclic allylic alcohols

A series of acyclic allylic alcohols were oxidised with catalytic osmium tetroxide. Use of dichloromethane as solvent and trimethylamine-N-oxide dihydrate as the reoxidant (Poli's conditions) gave levels of stereoselectivity that were superior to those found under more conventional oxidising conditions.