Issue 10, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
11 Dec 2018
Accepted
22 Jan 2019
First published
24 Jan 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 2875-2881

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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