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Synfacts 2009(7): 0749-0749  
DOI: 10.1055/s-0029-1217280
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Friedel-Crafts Alkylation of Indoles with a Cu-DNA Catalyst

Contributor(s): Mark Lautens, Praew Thansandote
A. J. Boersma, B. L. Feringa*, G. Roelfes*
University of Groningen, The Netherlands
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Publikationsdatum:
22. Juni 2009 (online)

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Significance

An impressive example of an enantioselective Friedel-Crafts reaction using water and a DNA-based catalyst is described. The catalyst is assembled in situ from Cu-dmbpy and salmon testes DNA, which is readily available and inexpensive. The reaction is compatible with a ­variety of substituents on the indole and olefin, ­although in some cases, using other DNA strands provided more optimal results. Results for both analytical and preparative scales are reported.