Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.

The iridium-catalyzed asym. hydrogenation of several N-sulfonyl allyl amines was reported. All substrates could be easily obtained by the Ir-catalyzed isomerization of N-tosylaziridines reported previously. The com. available threonine-derived phosphinite (UbaPHOX) iridium complex had been found to...

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Autores: Cabré Montesinos, Albert, Verdaguer i Espaulella, Xavier, Riera i Escalé, Antoni
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/143362
Acceso en línea:https://hdl.handle.net/2445/143362
Access Level:acceso abierto
Palabra clave:Iridi
Catàlisi asimètrica
Hidrogenació
Síntesi de fàrmacs
Iridium
Enantioselective catalysis
Hydrogenation
Drug synthesis
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spelling Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.Cabré Montesinos, AlbertVerdaguer i Espaulella, XavierRiera i Escalé, AntoniIridiCatàlisi asimètricaHidrogenacióSíntesi de fàrmacsIridiumEnantioselective catalysisHydrogenationDrug synthesisThe iridium-catalyzed asym. hydrogenation of several N-sulfonyl allyl amines was reported. All substrates could be easily obtained by the Ir-catalyzed isomerization of N-tosylaziridines reported previously. The com. available threonine-derived phosphinite (UbaPHOX) iridium complex had been found to be the best catalyst for this catalytic application, affording β-Me amines I [R1 = H, 4-Cl, 4-Br, etc.;R2 = Me, i-Pr, 4-MeC6H4; R3 = H, Me] with good to excellent ee values (up to 94%). The synthetic potential of this novel methodol. was demonstrated by the formal synthesis of Lorcaserin and LY-404187.Wiley-VCH2019info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/143362Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: https://doi.org/10.1002/adsc.201900748Advanced Synthesis & Catalysis, 2019, vol. 361, num. 18, p. 4196-4200https://doi.org/10.1002/adsc.201900748(c) Wiley-VCH, 2019info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1433622026-05-27T06:46:51Z
dc.title.none.fl_str_mv Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.
title Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.
spellingShingle Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.
Cabré Montesinos, Albert
Iridi
Catàlisi asimètrica
Hidrogenació
Síntesi de fàrmacs
Iridium
Enantioselective catalysis
Hydrogenation
Drug synthesis
title_short Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.
title_full Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.
title_fullStr Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.
title_full_unstemmed Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.
title_sort Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.
dc.creator.none.fl_str_mv Cabré Montesinos, Albert
Verdaguer i Espaulella, Xavier
Riera i Escalé, Antoni
author Cabré Montesinos, Albert
author_facet Cabré Montesinos, Albert
Verdaguer i Espaulella, Xavier
Riera i Escalé, Antoni
author_role author
author2 Verdaguer i Espaulella, Xavier
Riera i Escalé, Antoni
author2_role author
author
dc.subject.none.fl_str_mv Iridi
Catàlisi asimètrica
Hidrogenació
Síntesi de fàrmacs
Iridium
Enantioselective catalysis
Hydrogenation
Drug synthesis
topic Iridi
Catàlisi asimètrica
Hidrogenació
Síntesi de fàrmacs
Iridium
Enantioselective catalysis
Hydrogenation
Drug synthesis
description The iridium-catalyzed asym. hydrogenation of several N-sulfonyl allyl amines was reported. All substrates could be easily obtained by the Ir-catalyzed isomerization of N-tosylaziridines reported previously. The com. available threonine-derived phosphinite (UbaPHOX) iridium complex had been found to be the best catalyst for this catalytic application, affording β-Me amines I [R1 = H, 4-Cl, 4-Br, etc.;R2 = Me, i-Pr, 4-MeC6H4; R3 = H, Me] with good to excellent ee values (up to 94%). The synthetic potential of this novel methodol. was demonstrated by the formal synthesis of Lorcaserin and LY-404187.
publishDate 2019
dc.date.none.fl_str_mv 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/2445/143362
url https://hdl.handle.net/2445/143362
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/10.1002/adsc.201900748
Advanced Synthesis & Catalysis, 2019, vol. 361, num. 18, p. 4196-4200
https://doi.org/10.1002/adsc.201900748
dc.rights.none.fl_str_mv (c) Wiley-VCH, 2019
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Wiley-VCH, 2019
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 15,300719

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