Issue 18, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
08 Mar 2017
Accepted
18 Apr 2017
First published
18 Apr 2017

Org. Biomol. Chem., 2017,15, 4014-4021

[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, 15, 4014 DOI: 10.1039/C7OB00578D

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