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[3,3]-Sigmatropic rearrangement of allenic alcohols: stereoselective synthesis of 1,3-diene-2-ol sulfonates

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Abstract

An efficient synthetic pathway to 1,3-diene-2-ol sulfonates involving the [3,3]-sigmatropic rearrangement of allenic alcohols with sulfonic acids under mild reaction conditions is described. These products can easily undergo reduction or transition-metal catalyzed cross-coupling reactions to yield a series of stereodefined multisubstituted 1,3-dienes.

Graphical abstract: [3,3]-Sigmatropic rearrangement of allenic alcohols: stereoselective synthesis of 1,3-diene-2-ol sulfonates

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Publication details

The article was received on 08 Mar 2017, accepted on 18 Apr 2017 and first published on 18 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00578D
Citation: Org. Biomol. Chem., 2017, Advance Article
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    [3,3]-Sigmatropic rearrangement of allenic alcohols: stereoselective synthesis of 1,3-diene-2-ol sulfonates

    Y. Zhao, Y. Wang, Z. Gu and Z. Wang, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00578D

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