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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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Detalles Bibliográficos
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
Descripción
Sumario:[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.