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Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes
Author(s) -
Jinks Michael A.,
de Juan Alberto,
Denis Mathieu,
Fletcher Catherine J.,
Galli Marzia,
Jamieson Ellen M. G.,
Modicom Florian,
Zhang Zhihui,
Goldup Stephen M.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808990
Subject(s) - stereocenter , rotaxane , stereoselectivity , chemistry , covalent bond , stereochemistry , azide , molecule , enantioselective synthesis , organic chemistry , supramolecular chemistry , catalysis
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.