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

Christopher G. Nasveschuk; Tomislav Rovis

doi:10.1039/B714881J

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Organic & Biomolecular Chemistry

Issue 2, 2008

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

Christopher G. Nasveschuk and Tomislav Rovis

Org. Biomol. Chem., 2008, 6, 240-254

DOI: 10.1039/B714881J
Received 27 Sep 2007, First published on the web 04 Dec 2007

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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.

Abstract from Methods in Organic Synthesis 2008

A review, with 88 references, of the [1,3] rearrangement of vinyl ethers, focussing on mechanism and applications to stereoselective synthesis.

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Organic & Biomolecular Chemistry

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

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