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Issue 28, 2015
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DNA-cellulose: an economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis

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Abstract

The challenge in DNA-based asymmetric catalysis is to perform a reaction in the vicinity of the helix by incorporating a small-molecule catalyst anchored to the DNA in a covalent, dative, or non-covalent yet stable fashion in order to ensure high levels of enantio-discrimination. Here, we report the first generation of a DNA-based catalyst bound to a cellulose matrix. The chiral biomaterial is commercially available, trivial to use, fully recyclable and produces high levels of enantioselectivity in various Cu(II)-catalyzed asymmetric reactions including Friedel–Crafts alkylations and Michael additions. A single-pass, continuous-flow process is also reported affording fast conversions and high enantioselectivities at low catalyst loadings thus offering a new benchmark in the field of DNA-based asymmetric catalysis.

Graphical abstract: DNA-cellulose: an economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis

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Supplementary files

Article information


Submitted
20 Dec 2014
Accepted
11 Jan 2015
First published
14 Jan 2015

Chem. Commun., 2015,51, 6076-6079
Article type
Communication

DNA-cellulose: an economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis

E. Benedetti, N. Duchemin, L. Bethge, S. Vonhoff, S. Klussmann, J. Vasseur, J. Cossy, M. Smietana and S. Arseniyadis, Chem. Commun., 2015, 51, 6076
DOI: 10.1039/C4CC10190A

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