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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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Supplementary files

Article information


Submitted
26 Dec 2013
Accepted
24 Jan 2014
First published
31 Jan 2014

Chem. Sci., 2014,5, 1799-1803
Article type
Edge Article
Author version available

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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