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Issue 87, 2018
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Asymmetric synthesis via stereospecific C–N and C–O bond activation of alkyl amine and alcohol derivatives

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Abstract

This perspective showcases our development of benzylic and allylic amine and alcohol derivatives as electrophiles for stereospecific, nickel-catalyzed cross-coupling reactions, as well as the prior art that inspired our efforts. The success of our effort has relied on the use of benzyl ammonium triflates as electrophiles for cross-couplings via C–N bond activation and benzylic and allylic carboxylates for cross-couplings via C–O bond activation. Our work, along with others’ exciting discoveries, has demonstrated the potential of stereospecific, nickel-catalyzed cross-couplings of alkyl electrophiles in asymmetric synthesis, and enables efficient generation of both tertiary and quaternary stereocenters.

Graphical abstract: Asymmetric synthesis via stereospecific C–N and C–O bond activation of alkyl amine and alcohol derivatives

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Publication details

The article was received on 31 Aug 2018, accepted on 26 Sep 2018 and first published on 26 Sep 2018


Article type: Feature Article
DOI: 10.1039/C8CC07093H
Citation: Chem. Commun., 2018,54, 12286-12301

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    Asymmetric synthesis via stereospecific C–N and C–O bond activation of alkyl amine and alcohol derivatives

    S. M. Pound and M. P. Watson, Chem. Commun., 2018, 54, 12286
    DOI: 10.1039/C8CC07093H

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