title: Intra- and intermolecular 1,3-dipolar cycloaddition of sugar ketonitrones with mono-, di-, and trisubstituted dipolarophiles.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15782 Santiago, Spain. susana.torrente@ragactives.com
authors.forename: Susana
authors.initials: S
authors.lastname: Torrente
authors.forename: Beatriz
authors.initials: B
authors.lastname: Noya
authors.forename: Vicenç
authors.initials: V
authors.lastname: Branchadell
authors.forename: Ricardo
authors.initials: R
authors.lastname: Alonso
mesh_terms: 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
chemical_list: D002241:Carbohydrates; D007659:Ketones; D009589:Nitrogen Oxides; C015388:nitrones