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Issue 5, 2014
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Stereoselective construction of all-carbon quaternary center by means of chiral phosphoric acid: highly enantioselective Friedel–Crafts reaction of indoles with β,β-disubstituted nitroalkenes

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Abstract

We describe herein a chiral phosphoric acid catalyzed Friedel–Crafts reaction of indoles with β-alkoxycarbonyl-β-disubstituted nitroalkenes. A wide variety of substrates participated in this reaction to afford indoles having all-carbon quaternary centers with excellent selectivities (up to 97% ee). Further investigation suggested that the olefin geometry and the employment of NH-indole derivatives are responsible for both reactivity and selectivity.

Graphical abstract: Stereoselective construction of all-carbon quaternary center by means of chiral phosphoric acid: highly enantioselective Friedel–Crafts reaction of indoles with β,β-disubstituted nitroalkenes

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Publication details

The article was received on 26 Dec 2013, accepted on 24 Jan 2014 and first published on 31 Jan 2014


Article type: Edge Article
DOI: 10.1039/C3SC53542H
Author version available: Download Author version (PDF)
Citation: Chem. Sci., 2014,5, 1799-1803
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    Stereoselective construction of all-carbon quaternary center by means of chiral phosphoric acid: highly enantioselective Friedel–Crafts reaction of indoles with β,β-disubstituted nitroalkenes

    K. Mori, M. Wakazawa and T. Akiyama, Chem. Sci., 2014, 5, 1799
    DOI: 10.1039/C3SC53542H

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