Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation

A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported. The use of a CuCl (R,R)-Ph-Pybox catalyst system effects a simultaneous kinetic resolution of two racemic starting materials to give one majo...

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Autores principales: Brittain, William D. G., Dalling, Andrew G., Sun, Zhenquan, Duff, Cécile S. Le, Male, Louise, Buckley, Benjamin R., Fossey, John S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6803658/
https://www.ncbi.nlm.nih.gov/pubmed/31636274
http://dx.doi.org/10.1038/s41598-019-50940-4
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author Brittain, William D. G.
Dalling, Andrew G.
Sun, Zhenquan
Duff, Cécile S. Le
Male, Louise
Buckley, Benjamin R.
Fossey, John S.
author_facet Brittain, William D. G.
Dalling, Andrew G.
Sun, Zhenquan
Duff, Cécile S. Le
Male, Louise
Buckley, Benjamin R.
Fossey, John S.
author_sort Brittain, William D. G.
collection PubMed
description A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported. The use of a CuCl (R,R)-Ph-Pybox catalyst system effects a simultaneous kinetic resolution of two racemic starting materials to give one major triazolic diastereoisomer in the ratio 74:12:4:10 (dr 84:16, 90% ee maj). The corresponding control reaction using an achiral copper catalyst gives the four possible diastereoisomers in a 23:27:23:27 ratio, demonstrating minimal inherent substrate control.
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spelling pubmed-68036582019-10-24 Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation Brittain, William D. G. Dalling, Andrew G. Sun, Zhenquan Duff, Cécile S. Le Male, Louise Buckley, Benjamin R. Fossey, John S. Sci Rep Article A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported. The use of a CuCl (R,R)-Ph-Pybox catalyst system effects a simultaneous kinetic resolution of two racemic starting materials to give one major triazolic diastereoisomer in the ratio 74:12:4:10 (dr 84:16, 90% ee maj). The corresponding control reaction using an achiral copper catalyst gives the four possible diastereoisomers in a 23:27:23:27 ratio, demonstrating minimal inherent substrate control. Nature Publishing Group UK 2019-10-21 /pmc/articles/PMC6803658/ /pubmed/31636274 http://dx.doi.org/10.1038/s41598-019-50940-4 Text en © The Author(s) 2019 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
Brittain, William D. G.
Dalling, Andrew G.
Sun, Zhenquan
Duff, Cécile S. Le
Male, Louise
Buckley, Benjamin R.
Fossey, John S.
Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation
title Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation
title_full Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation
title_fullStr Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation
title_full_unstemmed Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation
title_short Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation
title_sort coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6803658/
https://www.ncbi.nlm.nih.gov/pubmed/31636274
http://dx.doi.org/10.1038/s41598-019-50940-4
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