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

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

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Animals
  • Catalysis
  • Cattle
  • Cellulose / chemistry*
  • Copper / chemistry*
  • DNA / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Organometallic Compounds
  • Copper
  • Cellulose
  • DNA
  • calf thymus DNA