Regioselectivity of vinyl sulfone based 1,3-dipolar cycloaddition reactions with sugar azides by computational and experimental studies.
DFT (M06-L) calculations on the transition state for the 1,3-dipolar cycloadditions between substituted vinyl sulfones with sugar azide have been reported in conjunction with new experimental results, and the origin of reversal of regioselectivity has been revealed using a distortion/interaction model. This study provides the scientific justification for combining organic azides with two different types of vinyl sulfones for the preparation of 1,5-disubstituted 1,2,3-triazoles and 1,4-disubstituted triazolyl esters under metal-free conditions.
Computation and Simulation Unit, Analytical Discipline & Centralized Instrument Facility, and Academy of Scientific and Innovative Research, CSIR-Central Salt and Marine Chemicals Research Institute , Bhavnagar, Gujarat 364002, India.
Debashis
D
Sahu
Santu
S
Dey
Tanmaya
T
Pathak
Bishwajit
B
Ganguly
D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D005697:Galactosides / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D001386:Azides; D005697:Galactosides; D013450:Sulfones; D014230:Triazoles; C009873:divinyl sulfone