Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst

A novel cationic [IrH(THF)(P,N)(imine)] [BArF] catalyst contg. a P-stereogenic MaxPHOX ligand is described for the direct asym. hydrogenation of N-Me and N-alkyl imines. This is the first catalytic system to attain high enantioselectivity (up to 94% ee) in this type of transformation. The labile THF...

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Autores: Salomó i Prat, Ernest, Gallen Ortiz, Albert, Sciortino, Giuseppe, Ujaque, Gregori, Grabulosa, Arnald, Lledós, Agustí (Lledós i Falcó), Riera i Escalé, Antoni, Verdaguer i Espaulella, Xavier
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/127015
Acceso en línea:https://hdl.handle.net/2445/127015
Access Level:acceso abierto
Palabra clave:Catàlisi asimètrica
Lligands
Hidrogenació
Enantioselective catalysis
Ligands
Hydrogenation
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spelling Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H CatalystSalomó i Prat, ErnestGallen Ortiz, AlbertSciortino, GiuseppeUjaque, GregoriGrabulosa, ArnaldLledós, Agustí (Lledós i Falcó)Riera i Escalé, AntoniVerdaguer i Espaulella, XavierCatàlisi asimètricaLligandsHidrogenacióEnantioselective catalysisLigandsHydrogenationA novel cationic [IrH(THF)(P,N)(imine)] [BArF] catalyst contg. a P-stereogenic MaxPHOX ligand is described for the direct asym. hydrogenation of N-Me and N-alkyl imines. This is the first catalytic system to attain high enantioselectivity (up to 94% ee) in this type of transformation. The labile THF ligand allows for effective activation and reactivity, even at low temps. D. functional theory calcns. allowed the rationalization of the stereochem. course of the reaction.American Chemical Society2018201920182018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion4 p.application/pdfhttps://hdl.handle.net/2445/127015Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: https://doi.org/10.1021/jacs.8b11547Journal of the American Chemical Society, 2018, vol. 140, p. 16967-16970https://doi.org/10.1021/jacs.8b11547(c) American Chemical Society , 2018info:eu-repo/semantics/openAccessoai:recercat.cat:2445/1270152026-05-29T05:05:01Z
dc.title.none.fl_str_mv Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst
title Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst
spellingShingle Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst
Salomó i Prat, Ernest
Catàlisi asimètrica
Lligands
Hidrogenació
Enantioselective catalysis
Ligands
Hydrogenation
title_short Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst
title_full Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst
title_fullStr Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst
title_full_unstemmed Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst
title_sort Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst
dc.creator.none.fl_str_mv Salomó i Prat, Ernest
Gallen Ortiz, Albert
Sciortino, Giuseppe
Ujaque, Gregori
Grabulosa, Arnald
Lledós, Agustí (Lledós i Falcó)
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author Salomó i Prat, Ernest
author_facet Salomó i Prat, Ernest
Gallen Ortiz, Albert
Sciortino, Giuseppe
Ujaque, Gregori
Grabulosa, Arnald
Lledós, Agustí (Lledós i Falcó)
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author_role author
author2 Gallen Ortiz, Albert
Sciortino, Giuseppe
Ujaque, Gregori
Grabulosa, Arnald
Lledós, Agustí (Lledós i Falcó)
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Catàlisi asimètrica
Lligands
Hidrogenació
Enantioselective catalysis
Ligands
Hydrogenation
topic Catàlisi asimètrica
Lligands
Hidrogenació
Enantioselective catalysis
Ligands
Hydrogenation
description A novel cationic [IrH(THF)(P,N)(imine)] [BArF] catalyst contg. a P-stereogenic MaxPHOX ligand is described for the direct asym. hydrogenation of N-Me and N-alkyl imines. This is the first catalytic system to attain high enantioselectivity (up to 94% ee) in this type of transformation. The labile THF ligand allows for effective activation and reactivity, even at low temps. D. functional theory calcns. allowed the rationalization of the stereochem. course of the reaction.
publishDate 2018
dc.date.none.fl_str_mv 2018
2018
2018
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/127015
url https://hdl.handle.net/2445/127015
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1021/jacs.8b11547
Journal of the American Chemical Society, 2018, vol. 140, p. 16967-16970
https://doi.org/10.1021/jacs.8b11547
dc.rights.none.fl_str_mv (c) American Chemical Society , 2018
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) American Chemical Society , 2018
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 4 p.
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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