Regioselectivity of Vinyl Sulfone Based 1,3-Dipolar Cycloaddition Reactions with Sugar Azides by Computational and Experimental Studies

• DOI: 10.1021/ol500461s
• Publication Date: 2014-04-03T18:05:23Z
• Authors: Debashis Sahu; Santu Dey; Tanmaya Pathak; Bishwajit Ganguly
• Keywords: Azides; Cycloaddition Reaction; Molecular Structure; Galactosides; Stereoisomerism; Triazoles; 01 natural sciences; Catalysis; 0104 chemical sciences; Models, Chemical; Cyclization; Sulfones

DFT (M06-L) calculations on the transition state for 1,3-dipolar cycloadditions between substituted vinyl sulfones with sugar azide have been reported in conjunction new experimental results, and origin of reversal regioselectivity has revealed using a distortion/interaction model. This study provides scientific justification combining organic azides two different types preparation 1,5-disubstituted 1,2,3-triazoles 1,4-disubstituted triazolyl esters under metal-free conditions.