Chemistry of β-Functionalized α-Nitroso Ethylenes. Methyl β-Nitroso Acrylate as Heterodienophile in [4 + 2]- Cycloaddition to Cyclic Dienes

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 und...

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Bibliographic Details
Published in:Organic letters 2000-05, Vol.2 (9), p.1323-1324
Main Authors: Tishkov, Alexander A, Lyapkalo, Il'ya M, Ioffe, Sema L, Strelenko, Yuri A, Tartakovsky, Vladimir A
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0057885