DNA-Based Catalytic Enantioselective Michael Reactions in Water†
David Coquière Dr.
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
Search for more papers by this authorBen L. Feringa Prof. Dr.
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
Search for more papers by this authorGerard Roelfes Dr.
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
Search for more papers by this authorDavid Coquière Dr.
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
Search for more papers by this authorBen L. Feringa Prof. Dr.
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
Search for more papers by this authorGerard Roelfes Dr.
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
Search for more papers by this authorWe thank A. J. Boersma for useful discussions and for providing the substrates, and the NRSC-Catalysis for financial support.
Graphical Abstract
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.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z703459_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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