Organic Letters
Organic Letters
5 years ago

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

A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane
Andreas W. Ehlers, Jan H. van Maarseveen, Martin J. Wanner, Luuk Steemers, Henk Hiemstra
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00877

DOI: 10.1021/acs.orglett.7b00877

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