Facial selectivities in the nucleophilic additions of 2,3-unsaturated 3-arylsulfinyl pyranosides.

Arunima Mukherjee, Narayanaswamy Jayaraman

Carbohydrate research 2013 Oct 18

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2,3-Unsaturated 3-arylsulfinyl pyranosides undergo nucleophilic additions at C-2, with facial selectivities depending on the nucleophile and the substituent on sulfinyl sulfur. The reactions of such sugar vinyl sulfoxides lead to the addition of nucleophile preferring an axial orientation at C-2, with concomitant formation of an allylic bond at C-3 to C-4. This trend in the addition pattern is observed for primary amine, carbon and sulfur nucleophiles, whereas secondary amines prefer an equatorial addition at C-2. The effect of p-tolylthio- versus (p-isopropylphenyl)thio vinyl sulfoxide is that the equatorial nucleophilic addition is preferred even more with the latter vinyl sulfoxide. Copyright © 2013. Published by Elsevier Ltd.

Citation

Arunima Mukherjee, Narayanaswamy Jayaraman. Facial selectivities in the nucleophilic additions of 2,3-unsaturated 3-arylsulfinyl pyranosides. Carbohydrate research. 2013 Oct 18;380:51-8