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Issue 2, 2008
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The [1, 3] O-to-C rearrangement: opportunities for stereoselective synthesis

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Abstract

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.

Graphical abstract: The [1, 3] O-to-C rearrangement: opportunities for stereoselective synthesis

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Publication details

The article was received on 27 Sep 2007 and first published on 04 Dec 2007


Article type: Perspective
DOI: 10.1039/B714881J
Org. Biomol. Chem., 2008,6, 240-254

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    The [1, 3] O-to-C rearrangement: opportunities for stereoselective synthesis

    C. G. Nasveschuk and T. Rovis, Org. Biomol. Chem., 2008, 6, 240
    DOI: 10.1039/B714881J

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