Stereoselective synthesis of mechanically planar chiral rotaxanes

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 a-am...

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Detalles Bibliográficos
Autores: Jinks, Michael A., Juan Garrudo, Alberto de, Denis, Mathieu, Fletcher, Catherine J., Galli, Marzia, Jamieson, Ellen M. G., Modicom, Florian, Zhang, Zhihui, Goldup, Stephen M.
Tipo de recurso: artículo
Fecha de publicación:2021
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/714026
Acceso en línea:http://hdl.handle.net/10486/714026
https://dx.doi.org/10.1002/anie.201808990
Access Level:acceso abierto
Palabra clave:Chirality
CuAAC
Rotaxane
Stereoselective synthesis
Supramolecular chemistry
Química
Descripción
Sumario: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 a-amino acid-derived azide. Symmetrization of the covalent stereocenter yields a rotaxane in which the mechanical bond provides the only stereogenic element