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Issue 17, 2010
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On the Role of DNA in DNA-based Catalytic Enantioselective Conjugate Addition Reactions

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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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Publication details

The article was received on 13 Apr 2010, accepted on 01 Jun 2010 and first published on 25 Jun 2010


Article type: Paper
DOI: 10.1039/C005048B
Citation: 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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