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
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spelling Stereoselective synthesis of mechanically planar chiral rotaxanesJinks, Michael A.Juan Garrudo, Alberto deDenis, MathieuFletcher, Catherine J.Galli, MarziaJamieson, Ellen M. G.Modicom, FlorianZhang, ZhihuiGoldup, Stephen M.ChiralityCuAACRotaxaneStereoselective synthesisSupramolecular chemistryQuímicaChiral 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 elementS.M.G. thanks the European Research Council (Consolidator Grant Agreement no. 724987), EPSRC (EP/L016621/1) and Leverhulme Trust (ORPG-2733) for fundingWileyDepartamento de Química OrgánicaFacultad de Ciencias20212021-11-21research articlehttp://purl.org/coar/resource_type/c_2df8fbb1VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10486/714026https://dx.doi.org/10.1002/anie.201808990reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/7140262026-06-23T12:46:27Z
dc.title.none.fl_str_mv Stereoselective synthesis of mechanically planar chiral rotaxanes
title Stereoselective synthesis of mechanically planar chiral rotaxanes
spellingShingle Stereoselective synthesis of mechanically planar chiral rotaxanes
Jinks, Michael A.
Chirality
CuAAC
Rotaxane
Stereoselective synthesis
Supramolecular chemistry
Química
title_short Stereoselective synthesis of mechanically planar chiral rotaxanes
title_full Stereoselective synthesis of mechanically planar chiral rotaxanes
title_fullStr Stereoselective synthesis of mechanically planar chiral rotaxanes
title_full_unstemmed Stereoselective synthesis of mechanically planar chiral rotaxanes
title_sort Stereoselective synthesis of mechanically planar chiral rotaxanes
dc.creator.none.fl_str_mv 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.
author Jinks, Michael A.
author_facet 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.
author_role author
author2 Juan Garrudo, Alberto de
Denis, Mathieu
Fletcher, Catherine J.
Galli, Marzia
Jamieson, Ellen M. G.
Modicom, Florian
Zhang, Zhihui
Goldup, Stephen M.
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Orgánica
Facultad de Ciencias
dc.subject.none.fl_str_mv Chirality
CuAAC
Rotaxane
Stereoselective synthesis
Supramolecular chemistry
Química
topic Chirality
CuAAC
Rotaxane
Stereoselective synthesis
Supramolecular chemistry
Química
description 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
publishDate 2021
dc.date.none.fl_str_mv 2021
2021-11-21
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10486/714026
https://dx.doi.org/10.1002/anie.201808990
url http://hdl.handle.net/10486/714026
https://dx.doi.org/10.1002/anie.201808990
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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