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Synfacts 2006(5): 0523-0523  
DOI: 10.1055/s-2006-934408
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

DNA-Based Catalysis

Contributor(s): Yasuhiro Uozumi, Maki Minakawa
G. Roelfes*, A. J. Boersma, B. L. Feringa*
University of Groningen, The Netherlands
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Publikationsdatum:
21. April 2006 (online)

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Significance

A new approach to DNA-based asymmetric catalysis gave very high enantioselectivities in the Cu(II)-catalyzed Diels-Alder reaction. The Diels-Alder reaction of cyclopentadiene 1 with dienophiles 2 catalyzed by DNA-based catalysts, assembled from salmon tests DNA (st-DNA) and [CuL(NO3)2] (L = 4-11), were performed at 5 °C for three days. The DNA is the source of chirality and the close contact between the DNA and the copper complex lead to the direct transfer of this chirality in the catalyzed reaction. As a result, complete regioselectivity (up to >99% endo) and excellent enantioselectivity (up to 99% ee) were observed in water.