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Issue 31, 2013
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Macrocycle synthesis by trimerization of boronic acids around a hexaol template, and recognition of polyols by resulting macrocyclic oligoboronic acids

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Abstract

2,6-Bis(alkenyloxy) substituted arylboronic acids can be cyclotrimerized with the help of a hexaol as a template. First, the boronic acids are assembled by boronic ester formation with hexahydroxy-bicyclo[2.2.2]octane. Next, the resulting triboronates are cyclized by ring-closing metathesis to yield trimacrocycles as diastereomeric E/Z mixtures. Catalytic hydrogenation yields a single saturated trimacrocycle. Cleavage of the boronic ester functions liberates the template and generates a macrocycle with three boronic acid functionalities in endo-orientation. Due to this preorganization, macrocycles with boronic acids in endo-positions are good receptors for polyols. The binding of carbohydrates such as fructose was compared with the uptake of the respective templates into macrocycles with two or three boronic acids in endo-orientation.

Graphical abstract: Macrocycle synthesis by trimerization of boronic acids around a hexaol template, and recognition of polyols by resulting macrocyclic oligoboronic acids

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Article information


Submitted
20 Mar 2013
Accepted
04 Jun 2013
First published
04 Jun 2013

Org. Biomol. Chem., 2013,11, 5109-5116
Article type
Paper

Macrocycle synthesis by trimerization of boronic acids around a hexaol template, and recognition of polyols by resulting macrocyclic oligoboronic acids

D. Stoltenberg and U. Lüning, Org. Biomol. Chem., 2013, 11, 5109
DOI: 10.1039/C3OB40554K

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