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Chem Commun (Camb). 2015 Apr 11;51(28):6076-9. doi: 10.1039/c4cc10190a.

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

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Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI) - ESPCI ParisTech/CNRS (UMR8231)/PSL* Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France.


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.

[Indexed for MEDLINE]

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