Issue 17, 2010
From the journal:

Organic & Biomolecular Chemistry

On the Role of DNA in DNA-based Catalytic Enantioselective Conjugate Addition Reactions†

Ewold W. Dijk,a   Arnold J. Boersma,a   Ben L. Feringa*a  and  Gerard Roelfes*a  

* Corresponding authors

a Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
E-mail: b.l.feringa@rug.nl, j.g.roelfes@rug.nl.
Fax: +31503634296

Abstract

A kinetic study of DNA-based catalytic enantioselective Friedel–Crafts alkylation and Michael addition reactions showed that DNA affects the rate of these reactions significantly. Whereas in the presence of DNA, a large acceleration was found for the Friedel–Crafts alkylation and a modest acceleration in the Michael addition of dimethyl malonate, a deceleration was observed when using nitromethane as nucleophile. Also, the enantioselectivities proved to be dependent on the DNA sequence. In comparison with the previously reported Diels–Alder reaction, the results presented here suggest that DNA plays a similar role in both cycloaddition and conjugate addition reactions.

Graphical abstract: On the Role of DNA in DNA-based Catalytic Enantioselective Conjugate Addition Reactions

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Article information

DOI
https://doi.org/10.1039/C005048B
Article type
Paper
Submitted
13 Apr 2010
Accepted
01 Jun 2010
First published
25 Jun 2010

Org. Biomol. Chem., 2010,8, 3868-3873

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On the Role of DNA in DNA-based Catalytic Enantioselective Conjugate Addition Reactions

E. W. Dijk, A. J. Boersma, B. L. Feringa and G. Roelfes, Org. Biomol. Chem., 2010, 8, 3868 DOI: 10.1039/C005048B

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