Double nucleophilic addition of bis(trimethylsilyl)ketene acetals to carbon-carbon double bonds of pyrazines: formation of polycyclic γ-lactones |
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| Authors: | Henri Rudler Bernard Denise Yiming Xu Jacqueline Vaissermann |
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| Institution: | Laboratoire de Chimie Organique, UMR 7611, Université Pierre et Marie Curie, T 44-45, Case 181, 4 place Jussieu, 75252 Paris Cedex 5, France |
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| Abstract: | The double activation of pyrazines upon their interaction with methyl chloroformate leading in the presence of bis(TMS)ketene acetals to polycyclic N-containing γ-lactones parallels the interaction of the same ketene acetals with metal-activated aromatics. The fundamental role of the two oxygen-silicon bonds is outlined. This result broadens the scope of application of these ketene acetals as potential 1,3-dinucleophiles. |
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| Keywords: | Pyrazines Ketene acetals Lactones |
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