Diastereoselective Amplification of a Mechanically Chiral [2]Catenane

J Am Chem Soc. 2021 Aug 11;143(31):11957-11962. doi: 10.1021/jacs.1c06557. Epub 2021 Jul 29.

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.

Publication types

  • Research Support, Non-U.S. Gov't