Publication: Thermolysis of imidates: A new method for the generation of carbonyl ylides
Thermolysis of imidates: A new method for the generation of carbonyl ylides
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Nikolaev, V. V., Linden, A., & Heimgartner, H. (2007). Thermolysis of imidates: A new method for the generation of carbonyl ylides. Helvetica Chimica Acta, 90(12), 2330–2341. https://doi.org/10.1002/hlca.200790239
Abstract
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Thermolysis of dimethyl 2-[(3-oxo-3H-isoindol-1-yl)oxy]malonate (8) promotes a [1,4]-H shift in the imidic N¼C O CH fragment of the starting molecule, which leads to a reactive carbonyl ylide. This carbonyl ylide can be trapped by the C¼N bond of imidates and imines, as well as the C¼O bond of benzaldehyde. The corresponding cycloadducts 11, 14, and 16 are formed regioselectively in good yields (60 – 95%) and with high stereoselectivity. In the case of 11, the minor cycloadduct in solution undergoes an isomerization to give the more
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- Nikolaev, V V
- Heimgartner, H
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Nikolaev, V. V., Linden, A., & Heimgartner, H. (2007). Thermolysis of imidates: A new method for the generation of carbonyl ylides. Helvetica Chimica Acta, 90(12), 2330–2341. https://doi.org/10.1002/hlca.200790239
