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Issue 10, 2019
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A rational quest for selectivity through precise ligand-positioning in tandem DNA-catalysed Friedel–Crafts alkylation/asymmetric protonation

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Abstract

Covalent anchorage of a metallic co-factor to a DNA-based architecture is merely the only way to ensure an accurate positioning of a catalytic site within the chiral micro-environment offered by the DNA double helix. Ultimately, it also allows a fine-tuning of the catalytic pocket through simple synthetic modifications of the DNA sequence. Here, we report highly selective copper(II)-catalysed asymmetric Friedel–Crafts conjugate addition/enantioselective protonation, which is due to a careful positioning of a bipyridine ligand within a DNA framework. Most importantly, this study unveils specific structural features that account for an optimal chirality transfer from the duplex to the Friedel–Crafts adducts.

Graphical abstract: A rational quest for selectivity through precise ligand-positioning in tandem DNA-catalysed Friedel–Crafts alkylation/asymmetric protonation

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Publication details

The article was received on 11 Dec 2018, accepted on 22 Jan 2019 and first published on 24 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05543B
Chem. Sci., 2019,10, 2875-2881
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    A rational quest for selectivity through precise ligand-positioning in tandem DNA-catalysed Friedel–Crafts alkylation/asymmetric protonation

    J. Mansot, S. Aubert, N. Duchemin, J. Vasseur, S. Arseniyadis and M. Smietana, Chem. Sci., 2019, 10, 2875
    DOI: 10.1039/C8SC05543B

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