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

Mukherjee, Arunima and Jayaraman, Narayanaswamy (2013) Facial selectivities in the nucleophilic additions of 2,3-unsaturated 3-arylsulfinyl pyranosides. In: CARBOHYDRATE RESEARCH, 380 . pp. 51-58.

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Official URL: http://dx.doi.org/10.1016/j.carres.2013.07.002

Abstract

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. (C) 2013 Published by Elsevier Ltd.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to Elesvier
Keywords: Conjugate additions; Nucleophiles; Stereoselective addition; Unsaturated sugars; Vinyl sulfoxides
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 29 Oct 2013 05:55
Last Modified: 29 Oct 2013 05:55
URI: http://eprints.iisc.ac.in/id/eprint/47609

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