Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolines

Chiral compounds containing nitrogen heteroatoms are fundamental substances for the chemical, pharmaceutical and agrochemical industries. However, the preparation of some of these interesting scaffolds is still underdeveloped. Herein we present the synthesis of a family of P-stereogenic phosphinooxa...

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Autores: Rojo, Pep, Molinari, Medea, Cabré Montesinos, Albert, García-Mateos, Clara, Riera i Escalé, Antoni, Verdaguer i Espaulella, Xavier
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/191334
Acceso en línea:https://hdl.handle.net/2445/191334
Access Level:acceso abierto
Palabra clave:Iridi
Hidrogenació
Lligands
Iridium
Hydrogenation
Ligands
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spelling Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolinesRojo, PepMolinari, MedeaCabré Montesinos, AlbertGarcía-Mateos, ClaraRiera i Escalé, AntoniVerdaguer i Espaulella, XavierIridiHidrogenacióLligandsIridiumHydrogenationLigandsChiral compounds containing nitrogen heteroatoms are fundamental substances for the chemical, pharmaceutical and agrochemical industries. However, the preparation of some of these interesting scaffolds is still underdeveloped. Herein we present the synthesis of a family of P-stereogenic phosphinooxazoline iridium catalysts from L-threonine methyl ester and their use in the asymmetric hydrogenation of N-Boc-2,3-diarylallyl amines, achieving very high enantioselectivity. Furthermore, the synthetic utility of the 2,3-diarylpropyl amines obtained is demonstrated by their transformation to 3-aryl-tetrahydroquinolines and 4-benzyl-tetrahydroisoquinolines, which have not yet been obtained in an enantioselective manner by direct reduction of the corresponding aromatic heterocycles. This strategy allows the preparation of these types of alkaloids with the highest enantioselectivity reported up to date.Wiley-VCH2022info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://hdl.handle.net/2445/191334Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésReproducció del document publicat a: https://doi.org/10.1002/anie.202204300Angewandte Chemie-International Edition, 2022, vol. 61, num. 29, p. 1-6https://doi.org/10.1002/anie.202204300cc-by (c) Rojo, Pep, et al., 2022http://creativecommons.org/licenses/by/3.0/es/info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1913342026-05-27T06:46:51Z
dc.title.none.fl_str_mv Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolines
title Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolines
spellingShingle Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolines
Rojo, Pep
Iridi
Hidrogenació
Lligands
Iridium
Hydrogenation
Ligands
title_short Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolines
title_full Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolines
title_fullStr Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolines
title_full_unstemmed Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolines
title_sort Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolines
dc.creator.none.fl_str_mv Rojo, Pep
Molinari, Medea
Cabré Montesinos, Albert
García-Mateos, Clara
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author Rojo, Pep
author_facet Rojo, Pep
Molinari, Medea
Cabré Montesinos, Albert
García-Mateos, Clara
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author_role author
author2 Molinari, Medea
Cabré Montesinos, Albert
García-Mateos, Clara
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Iridi
Hidrogenació
Lligands
Iridium
Hydrogenation
Ligands
topic Iridi
Hidrogenació
Lligands
Iridium
Hydrogenation
Ligands
description Chiral compounds containing nitrogen heteroatoms are fundamental substances for the chemical, pharmaceutical and agrochemical industries. However, the preparation of some of these interesting scaffolds is still underdeveloped. Herein we present the synthesis of a family of P-stereogenic phosphinooxazoline iridium catalysts from L-threonine methyl ester and their use in the asymmetric hydrogenation of N-Boc-2,3-diarylallyl amines, achieving very high enantioselectivity. Furthermore, the synthetic utility of the 2,3-diarylpropyl amines obtained is demonstrated by their transformation to 3-aryl-tetrahydroquinolines and 4-benzyl-tetrahydroisoquinolines, which have not yet been obtained in an enantioselective manner by direct reduction of the corresponding aromatic heterocycles. This strategy allows the preparation of these types of alkaloids with the highest enantioselectivity reported up to date.
publishDate 2022
dc.date.none.fl_str_mv 2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/191334
url https://hdl.handle.net/2445/191334
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: https://doi.org/10.1002/anie.202204300
Angewandte Chemie-International Edition, 2022, vol. 61, num. 29, p. 1-6
https://doi.org/10.1002/anie.202204300
dc.rights.none.fl_str_mv cc-by (c) Rojo, Pep, et al., 2022
http://creativecommons.org/licenses/by/3.0/es/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) Rojo, Pep, et al., 2022
http://creativecommons.org/licenses/by/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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