Straightforward Access to Enantioenriched cis-3-Fluoro-dihydroquinolin-4-ols Derivatives via Ru(II)-Catalyzed-Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution

Herein we report a practical method for the asymmetric transfer hydrogenation/dynamic kinetic resolution of N-Boc 3-fluoro-dihydrotetrahydroquinolin-4-ones into the corresponding cis-fluoro alcohols in 70–96% yields, up to 99:1 diastereomeric ratio (dr) and up to >99% ee (enantiomeric excess) by...

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Autores principales: Molina Betancourt, Ricardo, Phansavath, Phannarath, Ratovelomanana-Vidal, Virginie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8838918/
https://www.ncbi.nlm.nih.gov/pubmed/35164261
http://dx.doi.org/10.3390/molecules27030995
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author Molina Betancourt, Ricardo
Phansavath, Phannarath
Ratovelomanana-Vidal, Virginie
author_facet Molina Betancourt, Ricardo
Phansavath, Phannarath
Ratovelomanana-Vidal, Virginie
author_sort Molina Betancourt, Ricardo
collection PubMed
description Herein we report a practical method for the asymmetric transfer hydrogenation/dynamic kinetic resolution of N-Boc 3-fluoro-dihydrotetrahydroquinolin-4-ones into the corresponding cis-fluoro alcohols in 70–96% yields, up to 99:1 diastereomeric ratio (dr) and up to >99% ee (enantiomeric excess) by using the ruthenium complex Ts-DENEB and a formic acid/triethylamine (1:1) mixture as the hydrogen donor under mild conditions.
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spelling pubmed-88389182022-02-13 Straightforward Access to Enantioenriched cis-3-Fluoro-dihydroquinolin-4-ols Derivatives via Ru(II)-Catalyzed-Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution Molina Betancourt, Ricardo Phansavath, Phannarath Ratovelomanana-Vidal, Virginie Molecules Article Herein we report a practical method for the asymmetric transfer hydrogenation/dynamic kinetic resolution of N-Boc 3-fluoro-dihydrotetrahydroquinolin-4-ones into the corresponding cis-fluoro alcohols in 70–96% yields, up to 99:1 diastereomeric ratio (dr) and up to >99% ee (enantiomeric excess) by using the ruthenium complex Ts-DENEB and a formic acid/triethylamine (1:1) mixture as the hydrogen donor under mild conditions. MDPI 2022-02-01 /pmc/articles/PMC8838918/ /pubmed/35164261 http://dx.doi.org/10.3390/molecules27030995 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
Molina Betancourt, Ricardo
Phansavath, Phannarath
Ratovelomanana-Vidal, Virginie
Straightforward Access to Enantioenriched cis-3-Fluoro-dihydroquinolin-4-ols Derivatives via Ru(II)-Catalyzed-Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution
title Straightforward Access to Enantioenriched cis-3-Fluoro-dihydroquinolin-4-ols Derivatives via Ru(II)-Catalyzed-Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution
title_full Straightforward Access to Enantioenriched cis-3-Fluoro-dihydroquinolin-4-ols Derivatives via Ru(II)-Catalyzed-Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution
title_fullStr Straightforward Access to Enantioenriched cis-3-Fluoro-dihydroquinolin-4-ols Derivatives via Ru(II)-Catalyzed-Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution
title_full_unstemmed Straightforward Access to Enantioenriched cis-3-Fluoro-dihydroquinolin-4-ols Derivatives via Ru(II)-Catalyzed-Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution
title_short Straightforward Access to Enantioenriched cis-3-Fluoro-dihydroquinolin-4-ols Derivatives via Ru(II)-Catalyzed-Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution
title_sort straightforward access to enantioenriched cis-3-fluoro-dihydroquinolin-4-ols derivatives via ru(ii)-catalyzed-asymmetric transfer hydrogenation/dynamic kinetic resolution
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8838918/
https://www.ncbi.nlm.nih.gov/pubmed/35164261
http://dx.doi.org/10.3390/molecules27030995
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AT ratovelomananavidalvirginie straightforwardaccesstoenantioenrichedcis3fluorodihydroquinolin4olsderivativesviaruiicatalyzedasymmetrictransferhydrogenationdynamickineticresolution

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