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DNA-Based Catalytic Enantioselective Michael Reactions in Water

Authors

  • David Coquière Dr.,

    1. Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Fax: (+31) 50-363-4296
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  • Ben L. Feringa Prof. Dr.,

    1. Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Fax: (+31) 50-363-4296
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  • Gerard Roelfes Dr.

    1. Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Fax: (+31) 50-363-4296
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  • We thank A. J. Boersma for useful discussions and for providing the substrates, and the NRSC-Catalysis for financial support.

Abstract

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High, but not dry: A highly enantioselective Michael reaction in water has been developed by using a simple DNA-based catalyst. Enantioselectivities of up to 99 % ee could be obtained by using nitromethane and dimethyl malonate as the nucleophiles and α,β-unsaturated 2-acylimidazoles as the Michael acceptors. The reactions can be performed on a preparative scale and the catalyst can be recycled.

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