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Dr. Ashraf A. A. Abdel-Fattah :: Publications: |
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| Title: | Stereochemical aspects of novel 5,6-dihydro-4H-1,3-oxazines |
| Authors: | Alan R. Katritzky,a Ion Ghiviriga,b Ke Chen,a Dmytro O. Tymoshenko a and Ashraf A. A. Abdel-Fattah a |
| Year: | 2001 |
| Keywords: | Not Available |
| Journal: | J. Chem. Soc., Perkin Trans. |
| Volume: | 2 |
| Issue: | Not Available |
| Pages: | 530–537 |
| Publisher: | The Royal Society of Chemistry |
| Local/International: | International |
| Paper Link: | Not Available |
| Full paper | Ashraf Abdelfattah_Oxazines.pdf |
| 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. |
