Intra- and intermolecular 1,3-dipolar cycloaddition of sugar ketonitrones with mono-, di-, and trisubstituted dipolarophiles

J Org Chem. 2003 Jun 13;68(12):4772-83. doi: 10.1021/jo034159g.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemical synthesis
  • Carbohydrates / chemistry*
  • Combinatorial Chemistry Techniques*
  • Cyclization
  • Ketones / chemical synthesis
  • Ketones / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Nitrogen Oxides / chemical synthesis
  • Nitrogen Oxides / chemistry*
  • Thermodynamics

Substances

  • Carbohydrates
  • Ketones
  • Nitrogen Oxides
  • nitrones