Issue 28, 2015

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

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

Supplementary files

Article information

Article type
Communication
Submitted
20 Dec 2014
Accepted
11 Jan 2015
First published
14 Jan 2015

Chem. Commun., 2015,51, 6076-6079

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements