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A complementary pair of enantioselective switchable organocatalysts

A pair of enantioselective switchable bifunctional catalysts are shown to promote a range of conjugate addition reactions in up to 95 : 5 e.r. and 95% conversion. Each catalyst can be switched OFF using conditions that switch the other catalyst ON. Catalyst ON : OFF ratios of up to 98 : 2 and 1 : 99...

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Autores principales: De Bo, Guillaume, Leigh, David A., McTernan, Charlie T., Wang, Shoufeng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5637462/
https://www.ncbi.nlm.nih.gov/pubmed/29147536
http://dx.doi.org/10.1039/c7sc02462b
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author De Bo, Guillaume
Leigh, David A.
McTernan, Charlie T.
Wang, Shoufeng
author_facet De Bo, Guillaume
Leigh, David A.
McTernan, Charlie T.
Wang, Shoufeng
author_sort De Bo, Guillaume
collection PubMed
description A pair of enantioselective switchable bifunctional catalysts are shown to promote a range of conjugate addition reactions in up to 95 : 5 e.r. and 95% conversion. Each catalyst can be switched OFF using conditions that switch the other catalyst ON. Catalyst ON : OFF ratios of up to 98 : 2 and 1 : 99 were achieved, with a ratio of reaction rates of up to 16 : 1 between the ON and OFF states, maintained over complete ON–OFF–ON and OFF–ON–OFF cycles. However, simultaneous operation of the catalyst pair in the same reaction vessel, which in principle could allow product handedness to be switched by simple E–Z isomerisation of the catalyst pair, was unsuccessful. In this first generation complementary pair of enantioselective switchable organocatalysts, the OFF state of one catalyst inhibits the ON state of the other.
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spelling pubmed-56374622017-11-16 A complementary pair of enantioselective switchable organocatalysts De Bo, Guillaume Leigh, David A. McTernan, Charlie T. Wang, Shoufeng Chem Sci Chemistry A pair of enantioselective switchable bifunctional catalysts are shown to promote a range of conjugate addition reactions in up to 95 : 5 e.r. and 95% conversion. Each catalyst can be switched OFF using conditions that switch the other catalyst ON. Catalyst ON : OFF ratios of up to 98 : 2 and 1 : 99 were achieved, with a ratio of reaction rates of up to 16 : 1 between the ON and OFF states, maintained over complete ON–OFF–ON and OFF–ON–OFF cycles. However, simultaneous operation of the catalyst pair in the same reaction vessel, which in principle could allow product handedness to be switched by simple E–Z isomerisation of the catalyst pair, was unsuccessful. In this first generation complementary pair of enantioselective switchable organocatalysts, the OFF state of one catalyst inhibits the ON state of the other. Royal Society of Chemistry 2017-10-01 2017-08-23 /pmc/articles/PMC5637462/ /pubmed/29147536 http://dx.doi.org/10.1039/c7sc02462b Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
De Bo, Guillaume
Leigh, David A.
McTernan, Charlie T.
Wang, Shoufeng
A complementary pair of enantioselective switchable organocatalysts
title A complementary pair of enantioselective switchable organocatalysts
title_full A complementary pair of enantioselective switchable organocatalysts
title_fullStr A complementary pair of enantioselective switchable organocatalysts
title_full_unstemmed A complementary pair of enantioselective switchable organocatalysts
title_short A complementary pair of enantioselective switchable organocatalysts
title_sort complementary pair of enantioselective switchable organocatalysts
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5637462/
https://www.ncbi.nlm.nih.gov/pubmed/29147536
http://dx.doi.org/10.1039/c7sc02462b
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