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

ABSTRACT: 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.

SUBMITTER: Steemers L

PROVIDER: S-EPMC5423707 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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

Steemers Luuk L Wanner Martin J MJ Ehlers Andreas W AW Hiemstra Henk H van Maarseveen Jan H JH

Organic letters 20170424 9

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 connec ...[more]

PMID: 28437085

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