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Issue 12, 2014
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Regioselective and diastereoselective aminoarylation of 1,3-dienes

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Abstract

The 1,4-functionalization of dienes is a synthetically useful strategy for incorporating molecular complexity into a class of simple substrates. We report the aminoarylation of acyclic and cyclic 1,3-dienes via the sequential [4 + 2] cycloaddition with a sulfurdiimide reagent and copper-catalyzed allylic substitution with Grignard reagents. The regioselective and diastereoselective aminoarylation of unsymmetrical dienes is also presented, which highlights the utility of this method for generating products with multiple functional groups and stereocenters.

Graphical abstract: Regioselective and diastereoselective aminoarylation of 1,3-dienes

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Publication details

The article was received on 18 Apr 2014, accepted on 13 Aug 2014 and first published on 03 Sep 2014


Article type: Edge Article
DOI: 10.1039/C4SC01152J
Author version available: Download Author version (PDF)
Citation: Chem. Sci., 2014,5, 4863-4867
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    Regioselective and diastereoselective aminoarylation of 1,3-dienes

    H. Bao, L. Bayeh and U. K. Tambar, Chem. Sci., 2014, 5, 4863
    DOI: 10.1039/C4SC01152J

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