Dearomatization of furans via [2,3]-Still-Wittig rearrangement |
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Authors: | Patrick A. Caruana |
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Affiliation: | Department of Chemistry, University of Rochester, 414 Hutchison Hall, Rochester, NY 14627, USA |
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Abstract: | Furans and benzofurans of type 1 were dearomatized via the [2,3]-Still-Wittig rearrangement. Enol ethers 2 could be isolated or isomerized to the corresponding furans 3. The substitution pattern at the homofuranylic position had a strong influence on reaction behavior. Benzofurans rearranged with the greatest efficiency, and employment of a 3-substituted benzofuran (1; R′=CH3) allowed the creation of a quaternary carbon center. |
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Keywords: | [2,3]-Sigmatropic rearrangement Furans Heterocycles Dearomatization |
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