Intra- and intermolecular 1,3-dipolar cycloaddition of sugar ketonitrones with mono-, di-, and trisubstituted dipolarophiles.
The 1,3-dipolar cycloaddition of sugar ketonitrones is a useful synthetic procedure to build up nitrogenated quaternary centers in terms of scope (substrate, dipolarophile, inter- and intramolecular versions), yield, and regio- and stereoselectivity. The hybrid ONIOM (B3LYP/6-31G(d):AM1) theoretical method followed by single-point energy calculations at the B3LYP/6-31G(d) level adequately perform to model this cycloaddition for the relatively large ketosugar precursors commonly used.
Torrente
Susana
S
Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15782 Santiago, Spain. susana.torrente@ragactives.com
Noya
Beatriz
B
Branchadell
Vicenç
V
Alonso
Ricardo
R
D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D013816:Thermodynamics
D002241:Carbohydrates; D007659:Ketones; D009589:Nitrogen Oxides; C015388:nitrones