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Perspective
Org. Biomol. Chem., 2008, 6, 240 - 254, DOI: 10.1039/b714881j
The [1,
3] O-to-C rearrangement: opportunities for stereoselective synthesisChristopher G. Nasveschuk and Tomislav Rovis
The relay of stereochemistry of a breaking C–O bond into a forming C–C bond is well-known in the context of [3,
3] sigmatropic shifts; however, this useful strategy is less well-known in other types of molecular rearrangements. Though the first successful example of a [1,3] O-to-C rearrangement was reported more than 100 years ago, this class of reactions has received less attention than its [3,3] counterpart. This perspective analyzes the various methods used for the activation and [1,3] rearrangement of vinyl ethers with an emphasis on mechanism and applications to stereoselective synthesis. We also highlight our own contributions to this area.
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