Asymmetric synthesis using chiral-encoded metal

The synthesis of chiral compounds is of crucial importance in many areas of society and science, including medicine, biology, chemistry, biotechnology and agriculture. Thus, there is a fundamental interest in developing new approaches for the selective production of enantiomers. Here we report the u...

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Veröffentlicht in:Nature communications 2016-08, Vol.7 (1), p.12678-12678, Article 12678
Hauptverfasser: Yutthalekha, Thittaya, Wattanakit, Chularat, Lapeyre, Veronique, Nokbin, Somkiat, Warakulwit, Chompunuch, Limtrakul, Jumras, Kuhn, Alexander
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Sprache:eng
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Zusammenfassung:The synthesis of chiral compounds is of crucial importance in many areas of society and science, including medicine, biology, chemistry, biotechnology and agriculture. Thus, there is a fundamental interest in developing new approaches for the selective production of enantiomers. Here we report the use of mesoporous metal structures with encoded geometric chiral information for inducing asymmetry in the electrochemical synthesis of mandelic acid as a model molecule. The chiral-encoded mesoporous metal, obtained by the electrochemical reduction of platinum salts in the presence of a liquid crystal phase and the chiral template molecule, perfectly retains the chiral information after removal of the template. Starting from a prochiral compound we demonstrate enantiomeric excess of the ( R )-enantiomer when using ( R )-imprinted electrodes and vice versa for the ( S )-imprinted ones. Moreover, changing the amount of chiral cavities in the material allows tuning the enantioselectivity. Chiral compounds are extremely important as they can be used in medicine, agriculture and biotechnology. Here, Kuhn and co-workers use a mesoporous metal structure encoded with chiral information in order to induce asymmetry in electrochemical synthesis of mandelic acid.
ISSN:2041-1723
2041-1723
DOI:10.1038/ncomms12678