Abstract
X-Ray crystallographic analysis of an enantiopure 1-thio-α-D-glucopyranoside S-oxide clearly supports the role of the exo-anomeric effect in determining the highly stereoselective oxidation of α- thioglycosides to (RS) sulfoxides. Ab-initio and DFT calculations point out the relevance of the anomeric effect, due to the presence of sulfur at position 1, in determining some structural characteristics of aldohexosyl sulfoxides.
Keywords: anomeric effect, stereoselective oxidation, 1-thioglycosides
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