Gosteli-Claisen rearrangement of propargyl vinyl ethers: cascading molecular rearrangements |
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Authors: | Gille Annika Rehbein Julia Hiersemann Martin |
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Affiliation: | Fakulta?t Chemie, Technische Universita?t Dortmund, 44227 Dortmund, Germany. |
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Abstract: | The ambivalent reactivity of 2-alkoxycarbonyl-substituted propargyl vinyl ethers has been explored. Depending on the conditions, the catalyzed and uncatalyzed Gosteli-Claisen rearrangement triggers downstream transformations that cascade from initially formed γ-allenyl α-keto esters to highly substituted furanes and cyclopentenes. In support of a mechanistic hypothesis, the results of a DFT study using the B1B95 and B3LYP functionals are revealed. |
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