Asymmetric synthesis using chiral-encoded metal

Thittaya Yutthalekha, Chularat Wattanakit, Veronique Lapeyre, Somkiat Nokbin, Chompunuch Warakulwit, Jumras Limtrakul and Alexander Kuhn ()
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Thittaya Yutthalekha: Univ. Bordeaux, CNRS UMR 5255, Bordeaux INP, ENSCBP
Chularat Wattanakit: School of Energy Science and Engineering, Vidyasirimedhi Institute of Science and Technology
Veronique Lapeyre: Univ. Bordeaux, CNRS UMR 5255, Bordeaux INP, ENSCBP
Somkiat Nokbin: Faculty of Science, Kasetsart University
Chompunuch Warakulwit: Faculty of Science, Kasetsart University
Jumras Limtrakul: School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology
Alexander Kuhn: Univ. Bordeaux, CNRS UMR 5255, Bordeaux INP, ENSCBP

Nature Communications, 2016, vol. 7, issue 1, 1-8

Abstract: Abstract 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.

Date: 2016
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DOI: 10.1038/ncomms12678

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