| Autor: |
Tishkov, A. A., Lyapkalo, I. M., Ioffe, S. L., Strelenko, Y. A., Tartakovsky, V. A. |
| Zdroj: |
Organic Letters; May 2000, Vol. 2 Issue: 9 p1323-1324, 2p |
| Abstrakt: |
β-Functionalized nitroso alkene 2, obtained from methyl β-nitropropionate 1 and N,O-bis(trimethylsilyl)acetamide, can function as a good heterodienophile in Diels−Alder reactions. Therefore, 2 was trapped by cyclic dienes to give adducts 4 with the corresponding stereoselectivity. Cycloadduct 4a undergoes retro-[4 + 2]-cycloaddition at 33 °C in solution; thus 4a can be used to generate nitroso alkene 2 in neutral medium. Cyclopentadiene reacts with adduct 4a according to an endo-[4 + 2]-cycloaddition scheme to give cycloadduct 5 in low yield. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
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