Design and Synthesis of Pyrrolidinyl Ferrocene-Containing Ligands and Their Application in Highly Enantioselective Rhodium-Catalyzed Olefin Hydrogenation

Herein, we report the design and synthesis of a series of chiral pyrrolidine-substituted ferrocene-derived ligands. The proficiency of this novel structural motif was demonstrated in the Rh-catalyzed asymmetric hydrogenation of dehydroamino acid esters and α-aryl enamides. The products were obtained...

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Autores principales: Li, Xin, Brennan, Therese B., Kingston, Cian, Ortin, Yannick, Guiry, Patrick J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9505515/
https://www.ncbi.nlm.nih.gov/pubmed/36144811
http://dx.doi.org/10.3390/molecules27186078
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author Li, Xin
Brennan, Therese B.
Kingston, Cian
Ortin, Yannick
Guiry, Patrick J.
author_facet Li, Xin
Brennan, Therese B.
Kingston, Cian
Ortin, Yannick
Guiry, Patrick J.
author_sort Li, Xin
collection PubMed
description Herein, we report the design and synthesis of a series of chiral pyrrolidine-substituted ferrocene-derived ligands. The proficiency of this novel structural motif was demonstrated in the Rh-catalyzed asymmetric hydrogenation of dehydroamino acid esters and α-aryl enamides. The products were obtained with full conversions and excellent levels of enantioselectivities of up to >99.9% ee and 97.7% ee, respectively, using a BINOL-substituted phosphine-phosphoaramidite ligand which possesses planar, central, and axial chirality elements.
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spelling pubmed-95055152022-09-24 Design and Synthesis of Pyrrolidinyl Ferrocene-Containing Ligands and Their Application in Highly Enantioselective Rhodium-Catalyzed Olefin Hydrogenation Li, Xin Brennan, Therese B. Kingston, Cian Ortin, Yannick Guiry, Patrick J. Molecules Article Herein, we report the design and synthesis of a series of chiral pyrrolidine-substituted ferrocene-derived ligands. The proficiency of this novel structural motif was demonstrated in the Rh-catalyzed asymmetric hydrogenation of dehydroamino acid esters and α-aryl enamides. The products were obtained with full conversions and excellent levels of enantioselectivities of up to >99.9% ee and 97.7% ee, respectively, using a BINOL-substituted phosphine-phosphoaramidite ligand which possesses planar, central, and axial chirality elements. MDPI 2022-09-17 /pmc/articles/PMC9505515/ /pubmed/36144811 http://dx.doi.org/10.3390/molecules27186078 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Li, Xin
Brennan, Therese B.
Kingston, Cian
Ortin, Yannick
Guiry, Patrick J.
Design and Synthesis of Pyrrolidinyl Ferrocene-Containing Ligands and Their Application in Highly Enantioselective Rhodium-Catalyzed Olefin Hydrogenation
title Design and Synthesis of Pyrrolidinyl Ferrocene-Containing Ligands and Their Application in Highly Enantioselective Rhodium-Catalyzed Olefin Hydrogenation
title_full Design and Synthesis of Pyrrolidinyl Ferrocene-Containing Ligands and Their Application in Highly Enantioselective Rhodium-Catalyzed Olefin Hydrogenation
title_fullStr Design and Synthesis of Pyrrolidinyl Ferrocene-Containing Ligands and Their Application in Highly Enantioselective Rhodium-Catalyzed Olefin Hydrogenation
title_full_unstemmed Design and Synthesis of Pyrrolidinyl Ferrocene-Containing Ligands and Their Application in Highly Enantioselective Rhodium-Catalyzed Olefin Hydrogenation
title_short Design and Synthesis of Pyrrolidinyl Ferrocene-Containing Ligands and Their Application in Highly Enantioselective Rhodium-Catalyzed Olefin Hydrogenation
title_sort design and synthesis of pyrrolidinyl ferrocene-containing ligands and their application in highly enantioselective rhodium-catalyzed olefin hydrogenation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9505515/
https://www.ncbi.nlm.nih.gov/pubmed/36144811
http://dx.doi.org/10.3390/molecules27186078
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