Application of a lanthanide shift reagent in 17O n.m.r. spectroscopy to determine the stereochemical course of oxidation of cyclic sulphite diesters to cyclic sulphate diesters with ruthenium tetroxide

Abstract

Cyclic sulphite diesters are rapidly oxidized to cyclic sulphate diesters with ruthenium tetroside in good yield; diastereotopically labelled cyclic [¹⁷O] sulphate diesters obtained by oxidation of diastereoisomeric cyclic sulphite diesters with ruthenium [¹⁷O] tetroxide are shown, by the effect of a lanthanide shift reagent on their ¹⁷O n.m.r. signals, to be formed with retention of configuration at sulphur.