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Letters in Organic Chemistry

Author(s): Maria Chiara Aversa, Anna Barattucci, Paola Bonaccorsi, Giuseppe Bruno, Placido Giannetto and Patrick Rollin

DOI: 10.2174/1570178043400631

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The Role of the exo-Anomeric Effect in the Stereoselective Oxidation of 1- Thioglycosides: A Contribution in the α-D-Glucopyranoside Series Using XRay Crystallography

Page: [376 - 380] Pages: 5

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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