Stereoselective synthesis of β,γ-unsaturated- and β,γ-epoxy glycerol derivatives starting with glyceraldehyde and their use in the synthesis of alditols

Abstract

Highly stereoselective addition of vinylcopper and vinylcuprate compounds to glyceraldehyde acetonide affords both syn- and anti-β,γ-unsaturated glycerol derivatives, respectively, which can readily be converted into all the possible steric isomers of the β,γ-epoxy glycerol derivatives, which are useful intermediates in the synthesis of alditols.