Asymmetric Transfer Hydrogenation of Arylketones Catalyzed by Enantiopure Ruthenium(II)/Pybox Complexes Containing Achiral Phosphonite and Phosphinite Ligands

A family of complexes of the formula trans-[RuCl(2)(L)(R-pybox)] (R-pybox = (S,S)-(i)Pr-pybox, (R,R)-Ph-pybox, L = monodentate phosphonite, PPh(OR)(2), and phosphinite, L = PPh(2)(OR), ligands) were screened in the catalytic asymmetric transfer hydrogenation of acetophenone, observing a strong influ...

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Autores principales: Claros, Miguel, de Julián, Eire, Díez, Josefina, Lastra, Elena, Gamasa, M. Pilar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7070392/
https://www.ncbi.nlm.nih.gov/pubmed/32102166
http://dx.doi.org/10.3390/molecules25040990
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author Claros, Miguel
de Julián, Eire
Díez, Josefina
Lastra, Elena
Gamasa, M. Pilar
author_facet Claros, Miguel
de Julián, Eire
Díez, Josefina
Lastra, Elena
Gamasa, M. Pilar
author_sort Claros, Miguel
collection PubMed
description A family of complexes of the formula trans-[RuCl(2)(L)(R-pybox)] (R-pybox = (S,S)-(i)Pr-pybox, (R,R)-Ph-pybox, L = monodentate phosphonite, PPh(OR)(2), and phosphinite, L = PPh(2)(OR), ligands) were screened in the catalytic asymmetric transfer hydrogenation of acetophenone, observing a strong influence of the nature of both the R-pybox substituents and the L ligand in the process. The best results were obtained with complex trans-[RuCl(2){PPh(2)(OEt)}{(R,R)-Ph-pybox}] (2c), which provided high conversion and enantioselectivity (up to 96% enantiomeric excess, e.e.) for the reduction of a variety of aromatic ketones, affording the (S)-benzylalcohols.
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spelling pubmed-70703922020-03-19 Asymmetric Transfer Hydrogenation of Arylketones Catalyzed by Enantiopure Ruthenium(II)/Pybox Complexes Containing Achiral Phosphonite and Phosphinite Ligands Claros, Miguel de Julián, Eire Díez, Josefina Lastra, Elena Gamasa, M. Pilar Molecules Article A family of complexes of the formula trans-[RuCl(2)(L)(R-pybox)] (R-pybox = (S,S)-(i)Pr-pybox, (R,R)-Ph-pybox, L = monodentate phosphonite, PPh(OR)(2), and phosphinite, L = PPh(2)(OR), ligands) were screened in the catalytic asymmetric transfer hydrogenation of acetophenone, observing a strong influence of the nature of both the R-pybox substituents and the L ligand in the process. The best results were obtained with complex trans-[RuCl(2){PPh(2)(OEt)}{(R,R)-Ph-pybox}] (2c), which provided high conversion and enantioselectivity (up to 96% enantiomeric excess, e.e.) for the reduction of a variety of aromatic ketones, affording the (S)-benzylalcohols. MDPI 2020-02-23 /pmc/articles/PMC7070392/ /pubmed/32102166 http://dx.doi.org/10.3390/molecules25040990 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Claros, Miguel
de Julián, Eire
Díez, Josefina
Lastra, Elena
Gamasa, M. Pilar
Asymmetric Transfer Hydrogenation of Arylketones Catalyzed by Enantiopure Ruthenium(II)/Pybox Complexes Containing Achiral Phosphonite and Phosphinite Ligands
title Asymmetric Transfer Hydrogenation of Arylketones Catalyzed by Enantiopure Ruthenium(II)/Pybox Complexes Containing Achiral Phosphonite and Phosphinite Ligands
title_full Asymmetric Transfer Hydrogenation of Arylketones Catalyzed by Enantiopure Ruthenium(II)/Pybox Complexes Containing Achiral Phosphonite and Phosphinite Ligands
title_fullStr Asymmetric Transfer Hydrogenation of Arylketones Catalyzed by Enantiopure Ruthenium(II)/Pybox Complexes Containing Achiral Phosphonite and Phosphinite Ligands
title_full_unstemmed Asymmetric Transfer Hydrogenation of Arylketones Catalyzed by Enantiopure Ruthenium(II)/Pybox Complexes Containing Achiral Phosphonite and Phosphinite Ligands
title_short Asymmetric Transfer Hydrogenation of Arylketones Catalyzed by Enantiopure Ruthenium(II)/Pybox Complexes Containing Achiral Phosphonite and Phosphinite Ligands
title_sort asymmetric transfer hydrogenation of arylketones catalyzed by enantiopure ruthenium(ii)/pybox complexes containing achiral phosphonite and phosphinite ligands
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7070392/
https://www.ncbi.nlm.nih.gov/pubmed/32102166
http://dx.doi.org/10.3390/molecules25040990
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