Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

We herein report a method for the kinetic resolution of racemic 4-hydroxy[2.2]paracyclophane by means of a chiral isothiourea-catalyzed acylation with isobutyric anhydride. This protocol allows for a reasonable synthetically useful s-factor of 20 and provides a novel entry to obtain this interesting...

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Detalles Bibliográficos
Autores principales: Weinzierl, David, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8042488/
https://www.ncbi.nlm.nih.gov/pubmed/33889220
http://dx.doi.org/10.3762/bjoc.17.68
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author Weinzierl, David
Waser, Mario
author_facet Weinzierl, David
Waser, Mario
author_sort Weinzierl, David
collection PubMed
description We herein report a method for the kinetic resolution of racemic 4-hydroxy[2.2]paracyclophane by means of a chiral isothiourea-catalyzed acylation with isobutyric anhydride. This protocol allows for a reasonable synthetically useful s-factor of 20 and provides a novel entry to obtain this interesting planar chiral motive in an enantioenriched manner.
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spelling pubmed-80424882021-04-21 Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane Weinzierl, David Waser, Mario Beilstein J Org Chem Letter We herein report a method for the kinetic resolution of racemic 4-hydroxy[2.2]paracyclophane by means of a chiral isothiourea-catalyzed acylation with isobutyric anhydride. This protocol allows for a reasonable synthetically useful s-factor of 20 and provides a novel entry to obtain this interesting planar chiral motive in an enantioenriched manner. Beilstein-Institut 2021-04-08 /pmc/articles/PMC8042488/ /pubmed/33889220 http://dx.doi.org/10.3762/bjoc.17.68 Text en Copyright © 2021, Weinzierl and Waser https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Letter
Weinzierl, David
Waser, Mario
Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane
title Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane
title_full Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane
title_fullStr Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane
title_full_unstemmed Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane
title_short Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane
title_sort chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8042488/
https://www.ncbi.nlm.nih.gov/pubmed/33889220
http://dx.doi.org/10.3762/bjoc.17.68
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