Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes.

ABSTRACT: Chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit are typically produced with no control over the mechanical stereochemistry. Here we report a stereoselective approach to mechanically planar chiral rotaxanes in up to 98:2 d.r. using a readily available α-amino acid-derived azide. Symmetrization of the covalent stereocenter yields a rotaxane in which the mechanical bond provides the only stereogenic element.

SUBMITTER: Jinks MA 

PROVIDER: S-EPMC6220991 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature