P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversion

The synthesis of P-stereogenic bisphosphine ligands starting from a phosphinous acid chiral synthon and hydrazine is reported. The dialkylation of the hydrazine backbone yielded atropo- and nitrogeninversion isomers which are in slow exchange. The crystallization of one of the isomers allowed us to...

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Detalhes bibliográficos
Autores: Prades, Amparo, Núñez-Pertíñez, Samuel, Riera i Escalé, Antoni, Verdaguer i Espaulella, Xavier
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2017
País:España
Recursos: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:2445/110002
Acesso em linha:https://hdl.handle.net/2445/110002
Access Level:acceso abierto
Palavra-chave:Lligands
Catàlisi asimètrica
Ligands
Enantioselective catalysis
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spelling P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversionPrades, AmparoNúñez-Pertíñez, SamuelRiera i Escalé, AntoniVerdaguer i Espaulella, XavierLligandsCatàlisi asimètricaLigandsEnantioselective catalysisThe synthesis of P-stereogenic bisphosphine ligands starting from a phosphinous acid chiral synthon and hydrazine is reported. The dialkylation of the hydrazine backbone yielded atropo- and nitrogeninversion isomers which are in slow exchange. The crystallization of one of the isomers allowed us to study the reaction kinetics of the equilibria. The new ligands were tested in the Rh catalysed asymmetric hydrogenation of various benchmark substrates attaining up to 99% ee.Royal Society of Chemistry201720172017info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion20 p.application/pdfhttps://hdl.handle.net/2445/110002Articles 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)InglésReproducció del document publicat a: https://doi.org/10.1039/C7CC01944KChemical Communications, 2017, vol. 53, p. 4605-4608https://doi.org/10.1039/C7CC01944KCC BY (c) Prades, Amparo et al., 2017http://creativecommons.org/licenses/by/3.0/info:eu-repo/semantics/openAccessoai:recercat.cat:2445/1100022026-05-29T05:05:01Z
dc.title.none.fl_str_mv P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversion
title P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversion
spellingShingle P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversion
Prades, Amparo
Lligands
Catàlisi asimètrica
Ligands
Enantioselective catalysis
title_short P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversion
title_full P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversion
title_fullStr P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversion
title_full_unstemmed P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversion
title_sort P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversion
dc.creator.none.fl_str_mv Prades, Amparo
Núñez-Pertíñez, Samuel
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author Prades, Amparo
author_facet Prades, Amparo
Núñez-Pertíñez, Samuel
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author_role author
author2 Núñez-Pertíñez, Samuel
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author2_role author
author
author
dc.subject.none.fl_str_mv Lligands
Catàlisi asimètrica
Ligands
Enantioselective catalysis
topic Lligands
Catàlisi asimètrica
Ligands
Enantioselective catalysis
description The synthesis of P-stereogenic bisphosphine ligands starting from a phosphinous acid chiral synthon and hydrazine is reported. The dialkylation of the hydrazine backbone yielded atropo- and nitrogeninversion isomers which are in slow exchange. The crystallization of one of the isomers allowed us to study the reaction kinetics of the equilibria. The new ligands were tested in the Rh catalysed asymmetric hydrogenation of various benchmark substrates attaining up to 99% ee.
publishDate 2017
dc.date.none.fl_str_mv 2017
2017
2017
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/2445/110002
url https://hdl.handle.net/2445/110002
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/10.1039/C7CC01944K
Chemical Communications, 2017, vol. 53, p. 4605-4608
https://doi.org/10.1039/C7CC01944K
dc.rights.none.fl_str_mv CC BY (c) Prades, Amparo et al., 2017
http://creativecommons.org/licenses/by/3.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv CC BY (c) Prades, Amparo et al., 2017
http://creativecommons.org/licenses/by/3.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 20 p.
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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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