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Issue 2, 2017
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Highly enantioselective metallation–substitution alpha to a chiral nitrile

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Abstract

We report the deprotonation of a chiral nitrile and reaction of the resulting chiral organometallic species with a variety of electrophiles to give highly enantiomerically enriched 2-substituted nitrile products. The nitrile was treated with TMPMgCl and the resulting anion, an asymmetric alpha cyano Grignard species, was found to be configurationally stable at low temperature for a short time (half-life several minutes at −104 °C).

Graphical abstract: Highly enantioselective metallation–substitution alpha to a chiral nitrile

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Publication details

The article was received on 18 Aug 2016, accepted on 24 Oct 2016 and first published on 25 Oct 2016


Article type: Edge Article
DOI: 10.1039/C6SC03712G
Citation: Chem. Sci., 2017,8, 1436-1441
  • Open access: Creative Commons BY license
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    Highly enantioselective metallation–substitution alpha to a chiral nitrile

    A. Sadhukhan, M. C. Hobbs, A. J. H. M. Meijer and I. Coldham, Chem. Sci., 2017, 8, 1436
    DOI: 10.1039/C6SC03712G

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