DNA-Based Catalytic Enantioselective Michael Reactions in Water

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2007-01, Vol.46 (48), p.9308-9311
Main Authors: Coquière, David, Feringa, Ben L., Roelfes, Gerard
Format: Article
Language:English
Subjects:
asymmetric catalysis
Catalysis
copper
DNA
DNA - chemistry
Imidazoles - chemistry
Malonates - chemistry
Methane - analogs & derivatives
Methane - chemistry
Michael addition
Molecular Conformation
Nitroparaffins - chemistry
Water - chemistry
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200703459