- Diastereoselective Amplification of a Mechanically Chiral [2]Catenane
Caprice, K.; Pál, D.; Besnard, C.; Galmés, B.; Frontera, A.; Cougnon, F. B. L.
J. Am. Chem. Soc. 2021, 143, 11957-11962
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.
DOI : 10.1021/jacs.1c06557
archive ouverte unige:153947
