Enantiomerically pure β,γ-epoxyesters from β-hydroxylactones: Synthesis of β-hydroxyesters and (-)-GABOB

Article abstract of DOI:10.1016/S0040-4020(01)86765-X

The preparation of enantiomerically pure β,γ-epoxyesters was achieved by chemoselective opening of β-hydroxybutanolides with trimethylsilyliodide followed by cyclisation of the resulting iodohydrins with silver oxide. The reaction of these epoxyesters with lithio or magnesiocuprates afforded stereochemically pure α-substituted β-hydroxyesters. Alternatively, (-)-GABOB was synthesized in optically pure form from the iodohydrin 2′a.