Format

Send to

Choose Destination
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.

Author information

1
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. stellios.arseniyadis@espci.fr.

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.

PMID:
25613918
DOI:
10.1039/c4cc10190a
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for Royal Society of Chemistry
Loading ...
Support Center