A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane

[Image: see text] While the current supramolecular syntheses of [2]rotaxanes are generally efficient, the final product always retains the functional groups required for non-covalent preorganization. A short and high-yielding covalent-template-assisted approach is reported for the synthesis of a [2]...

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Autores principales: Steemers, Luuk, Wanner, Martin J., Ehlers, Andreas W., Hiemstra, Henk, van Maarseveen, Jan H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5423707/
https://www.ncbi.nlm.nih.gov/pubmed/28437085
http://dx.doi.org/10.1021/acs.orglett.7b00877
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author Steemers, Luuk
Wanner, Martin J.
Ehlers, Andreas W.
Hiemstra, Henk
van Maarseveen, Jan H.
author_facet Steemers, Luuk
Wanner, Martin J.
Ehlers, Andreas W.
Hiemstra, Henk
van Maarseveen, Jan H.
author_sort Steemers, Luuk
collection PubMed
description [Image: see text] While the current supramolecular syntheses of [2]rotaxanes are generally efficient, the final product always retains the functional groups required for non-covalent preorganization. A short and high-yielding covalent-template-assisted approach is reported for the synthesis of a [2]rotaxane. A terephthalic acid template core preorganizes the covalently connected ring precursor fragments to induce a clipping-type cyclization over the thread moiety. Cleavage of the temporary ester bonds that connect the ring and thread fragments liberates the [2]rotaxane.
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spelling pubmed-54237072017-05-10 A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane Steemers, Luuk Wanner, Martin J. Ehlers, Andreas W. Hiemstra, Henk van Maarseveen, Jan H. Org Lett [Image: see text] While the current supramolecular syntheses of [2]rotaxanes are generally efficient, the final product always retains the functional groups required for non-covalent preorganization. A short and high-yielding covalent-template-assisted approach is reported for the synthesis of a [2]rotaxane. A terephthalic acid template core preorganizes the covalently connected ring precursor fragments to induce a clipping-type cyclization over the thread moiety. Cleavage of the temporary ester bonds that connect the ring and thread fragments liberates the [2]rotaxane. American Chemical Society 2017-04-24 2017-05-05 /pmc/articles/PMC5423707/ /pubmed/28437085 http://dx.doi.org/10.1021/acs.orglett.7b00877 Text en Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Steemers, Luuk
Wanner, Martin J.
Ehlers, Andreas W.
Hiemstra, Henk
van Maarseveen, Jan H.
A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane
title A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane
title_full A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane
title_fullStr A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane
title_full_unstemmed A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane
title_short A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane
title_sort short covalent synthesis of an all-carbon-ring [2]rotaxane
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5423707/
https://www.ncbi.nlm.nih.gov/pubmed/28437085
http://dx.doi.org/10.1021/acs.orglett.7b00877
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