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Issue 6, 2010
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Organic co-solvents in aqueous DNA-based asymmetric catalysis

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Abstract

Water-miscible organic co-solvents can be used in DNA-based catalytic asymmetric reactions at appreciable concentration without a negative effect on enantioselectivity. While the rate of the copper(II) Diels–Alder reaction is affected negatively by the presence of organic co-solvents, the copper(II) catalyzed Michael addition and Friedel–Crafts alkylation reaction are significantly faster. Additionally, the presence of organic co-solvents allows for reaction temperatures <0 °C, which results in higher ee's. This is used to perform enantioselective Michael additions and Friedel–Crafts alkylations at gram scale, using catalyst loadings as low as 0.75 mol%. These results are an important step towards application of the DNA-based catalysis concept in organic synthesis

Graphical abstract: Organic co-solvents in aqueous DNA-based asymmetric catalysis

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Supplementary files

Article information


Submitted
13 Oct 2009
Accepted
17 Dec 2009
First published
15 Jan 2010

Org. Biomol. Chem., 2010,8, 1387-1393
Article type
Paper

Organic co-solvents in aqueous DNA-based asymmetric catalysis

R. P. Megens and G. Roelfes, Org. Biomol. Chem., 2010, 8, 1387
DOI: 10.1039/B921385F

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