Memory of chirality in a room temperature flow electrochemical reactor

Abstract Chiral compounds have become of great interest to the pharmaceutical industry as they possess various biological activities. Concurrently, the concept of “memory of chirality” has been proven as a powerful tool in asymmetric synthesis, while flow chemistry has begun its rise as a new enabli...

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Autores principales:	Tomas Hardwick, Rossana Cicala, Nisar Ahmed
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2020
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/cd1c0ae215e843c2934b64b6dd345e4d
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spelling	oai:doaj.org-article:cd1c0ae215e843c2934b64b6dd345e4d2021-12-02T18:37:06ZMemory of chirality in a room temperature flow electrochemical reactor10.1038/s41598-020-73957-62045-2322https://doaj.org/article/cd1c0ae215e843c2934b64b6dd345e4d2020-10-01T00:00:00Zhttps://doi.org/10.1038/s41598-020-73957-6https://doaj.org/toc/2045-2322Abstract Chiral compounds have become of great interest to the pharmaceutical industry as they possess various biological activities. Concurrently, the concept of “memory of chirality” has been proven as a powerful tool in asymmetric synthesis, while flow chemistry has begun its rise as a new enabling technology to add to the ever increasing arsenal of techniques available to the modern day chemist. Here, we have employed a new simple electrochemical microreactor design to oxidise an l-proline derivative at room temperature in continuous flow. Compared to batch, organic electrosynthesis via microflow reactors are advantageous because they allow shorter reaction times, optimization and scale up, safer working environments, and high selectivities (e.g. reduce overoxidation). Flow electrochemical reactors also provide high surface-to-volume ratios and impart the possibility of excluding the supporting electrolyte due to a very short interelectrode distance. By the comparison of Hofer Moest type electrochemical oxidations at room temperature in batch and flow, we conclude that continuous flow electrolysis is superior to batch, producing a good yield (71%) and a higher enantiomeric excess (64%). These results show that continuous flow has the potential to act as a new enabling technology for asymmetric synthesis to replace some aspects of conventional batch electrochemical processes.Tomas HardwickRossana CicalaNisar AhmedNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 10, Iss 1, Pp 1-8 (2020)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Tomas Hardwick Rossana Cicala Nisar Ahmed Memory of chirality in a room temperature flow electrochemical reactor
description	Abstract Chiral compounds have become of great interest to the pharmaceutical industry as they possess various biological activities. Concurrently, the concept of “memory of chirality” has been proven as a powerful tool in asymmetric synthesis, while flow chemistry has begun its rise as a new enabling technology to add to the ever increasing arsenal of techniques available to the modern day chemist. Here, we have employed a new simple electrochemical microreactor design to oxidise an l-proline derivative at room temperature in continuous flow. Compared to batch, organic electrosynthesis via microflow reactors are advantageous because they allow shorter reaction times, optimization and scale up, safer working environments, and high selectivities (e.g. reduce overoxidation). Flow electrochemical reactors also provide high surface-to-volume ratios and impart the possibility of excluding the supporting electrolyte due to a very short interelectrode distance. By the comparison of Hofer Moest type electrochemical oxidations at room temperature in batch and flow, we conclude that continuous flow electrolysis is superior to batch, producing a good yield (71%) and a higher enantiomeric excess (64%). These results show that continuous flow has the potential to act as a new enabling technology for asymmetric synthesis to replace some aspects of conventional batch electrochemical processes.
format	article
author	Tomas Hardwick Rossana Cicala Nisar Ahmed
author_facet	Tomas Hardwick Rossana Cicala Nisar Ahmed
author_sort	Tomas Hardwick
title	Memory of chirality in a room temperature flow electrochemical reactor
title_short	Memory of chirality in a room temperature flow electrochemical reactor
title_full	Memory of chirality in a room temperature flow electrochemical reactor
title_fullStr	Memory of chirality in a room temperature flow electrochemical reactor
title_full_unstemmed	Memory of chirality in a room temperature flow electrochemical reactor
title_sort	memory of chirality in a room temperature flow electrochemical reactor
publisher	Nature Portfolio
publishDate	2020
url	https://doaj.org/article/cd1c0ae215e843c2934b64b6dd345e4d
work_keys_str_mv	AT tomashardwick memoryofchiralityinaroomtemperatureflowelectrochemicalreactor AT rossanacicala memoryofchiralityinaroomtemperatureflowelectrochemicalreactor AT nisarahmed memoryofchiralityinaroomtemperatureflowelectrochemicalreactor
_version_	1718377826191671296

Memory of chirality in a room temperature flow electrochemical reactor

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