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Diastereoselective Amplification of a Mechanically Chiral [2]Catenane

Galmés, Bartomeu
Frontera, Antonio
Published in Journal of the American Chemical Society. 2021, vol. 143, no. 31, p. 11957-11962
Abstract Achiral [2]catenanes composed of rings with inequivalent sides may adopt chiral co-conformations. Their stereochemistry depends on the relative orientation of the interlocked rings and can be controlled by sterics or an external stimulus (e.g., a chemical stimulus). Herein, we have exploited this stereodynamic property to amplify a mechanically chiral (P)-catenane upon binding to (R)-1,1′-binaphthyl 2,2′-disulfonate, with a diastereomeric excess of 85%. The chirality of the [2]catenane was ascertained in the solid state by single crystal X-ray diffraction and in solution by NMR and CD spectroscopies. This study establishes a robust basis for the development of a new synthetic approach to access enantioenriched mechanically chiral [2]catenanes.
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Research group Groupe Cougnon
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CAPRICE, Kenji et al. Diastereoselective Amplification of a Mechanically Chiral [2]Catenane. In: Journal of the American Chemical Society, 2021, vol. 143, n° 31, p. 11957-11962. doi: 10.1021/jacs.1c06557 https://archive-ouverte.unige.ch/unige:153947

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Deposited on : 2021-08-18

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