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Stereochemical aspects of novel 5,6-dihydro-4H-1,3-oxazines
J. Chem. Soc., Perkin Trans. • 2001
Publication Information
Authors
Alan R. Katritzky,a Ion Ghiviriga,b Ke Chen,a Dmytro O. Tymoshenko a and
Ashraf A. A. Abdel-Fattah a
Keywords
Not Available
Journal
J. Chem. Soc., Perkin Trans.
Publisher
The Royal Society of Chemistry
Volume
2
Issue
Not Available
Pages
530–537
publication.type
International
Paper Link
Not Available
Supplementary Materials
Not Available
Abstract
Novel polysubstituted 5,6-dihydro-4H-1,3-oxazines are synthesized by 1,4-cycloaddition of unactivated olefins
with N-acyliminiums from benzotriazole precursors. The configuration and conformation of the products are
deduced from NMR investigation. The regio- and exo–endo stereochemistry of the cycloaddition are discussed.
Conformations of compounds of six types of substitution (6-mono; 6,6-, 5,6- and 4,6-di; 4,6,6- and 4,5,6-tri)
are rationalized on the basis of axial-1,3-repulsion and the anomeric effect.
with N-acyliminiums from benzotriazole precursors. The configuration and conformation of the products are
deduced from NMR investigation. The regio- and exo–endo stereochemistry of the cycloaddition are discussed.
Conformations of compounds of six types of substitution (6-mono; 6,6-, 5,6- and 4,6-di; 4,6,6- and 4,5,6-tri)
are rationalized on the basis of axial-1,3-repulsion and the anomeric effect.