Cargando…

Pulsed electroconversion for highly selective enantiomer synthesis

Asymmetric synthesis of molecules is of crucial importance to obtain pure chiral compounds, which are of primary interest in many areas including medicine, biotechnology, and chemistry. Various methods have been used very successfully to increase the enantiomeric yield of reaction pathways, but ther...

Descripción completa

Detalles Bibliográficos
Autores principales: Wattanakit, Chularat, Yutthalekha, Thittaya, Asssavapanumat, Sunpet, Lapeyre, Veronique, Kuhn, Alexander
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5727193/
https://www.ncbi.nlm.nih.gov/pubmed/29233998
http://dx.doi.org/10.1038/s41467-017-02190-z
_version_ 1783285827261956096
author Wattanakit, Chularat
Yutthalekha, Thittaya
Asssavapanumat, Sunpet
Lapeyre, Veronique
Kuhn, Alexander
author_facet Wattanakit, Chularat
Yutthalekha, Thittaya
Asssavapanumat, Sunpet
Lapeyre, Veronique
Kuhn, Alexander
author_sort Wattanakit, Chularat
collection PubMed
description Asymmetric synthesis of molecules is of crucial importance to obtain pure chiral compounds, which are of primary interest in many areas including medicine, biotechnology, and chemistry. Various methods have been used very successfully to increase the enantiomeric yield of reaction pathways, but there is still room for the development of alternative highly enantioselective reaction concepts, either as a scientific challenge of tremendous fundamental significance, or owing to the increasing demand for enantiopure products, e.g., in the pharmaceutical industry. In this context, we report here a strategy for the synthesis of chiral compounds, based on pulsed electrochemical conversion. We illustrate the approach with the stereospecific electroreduction of a prochiral model molecule at chiral mesoporous metal structures, resulting in an enantiomeric excess of over 90%. This change of paradigm opens up promising reaction schemes for the straightforward synthesis of high-added-value molecules.
format Online
Article
Text
id pubmed-5727193
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-57271932017-12-14 Pulsed electroconversion for highly selective enantiomer synthesis Wattanakit, Chularat Yutthalekha, Thittaya Asssavapanumat, Sunpet Lapeyre, Veronique Kuhn, Alexander Nat Commun Article Asymmetric synthesis of molecules is of crucial importance to obtain pure chiral compounds, which are of primary interest in many areas including medicine, biotechnology, and chemistry. Various methods have been used very successfully to increase the enantiomeric yield of reaction pathways, but there is still room for the development of alternative highly enantioselective reaction concepts, either as a scientific challenge of tremendous fundamental significance, or owing to the increasing demand for enantiopure products, e.g., in the pharmaceutical industry. In this context, we report here a strategy for the synthesis of chiral compounds, based on pulsed electrochemical conversion. We illustrate the approach with the stereospecific electroreduction of a prochiral model molecule at chiral mesoporous metal structures, resulting in an enantiomeric excess of over 90%. This change of paradigm opens up promising reaction schemes for the straightforward synthesis of high-added-value molecules. Nature Publishing Group UK 2017-12-12 /pmc/articles/PMC5727193/ /pubmed/29233998 http://dx.doi.org/10.1038/s41467-017-02190-z Text en © The Author(s) 2017 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Wattanakit, Chularat
Yutthalekha, Thittaya
Asssavapanumat, Sunpet
Lapeyre, Veronique
Kuhn, Alexander
Pulsed electroconversion for highly selective enantiomer synthesis
title Pulsed electroconversion for highly selective enantiomer synthesis
title_full Pulsed electroconversion for highly selective enantiomer synthesis
title_fullStr Pulsed electroconversion for highly selective enantiomer synthesis
title_full_unstemmed Pulsed electroconversion for highly selective enantiomer synthesis
title_short Pulsed electroconversion for highly selective enantiomer synthesis
title_sort pulsed electroconversion for highly selective enantiomer synthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5727193/
https://www.ncbi.nlm.nih.gov/pubmed/29233998
http://dx.doi.org/10.1038/s41467-017-02190-z
work_keys_str_mv AT wattanakitchularat pulsedelectroconversionforhighlyselectiveenantiomersynthesis
AT yutthalekhathittaya pulsedelectroconversionforhighlyselectiveenantiomersynthesis
AT asssavapanumatsunpet pulsedelectroconversionforhighlyselectiveenantiomersynthesis
AT lapeyreveronique pulsedelectroconversionforhighlyselectiveenantiomersynthesis
AT kuhnalexander pulsedelectroconversionforhighlyselectiveenantiomersynthesis