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Room-Temperature Asymmetric Transfer Hydrogenation of Biomass-Derived Levulinic Acid to Optically Pure γ-Valerolactone Using a Ruthenium Catalyst

[Image: see text] This study presents a first report on ruthenium-catalyzed asymmetric transfer hydrogenation (ATH) of levulinic acid (LA) to chiral γ-valerolactone (GVL). ATH of LA has been explored with Noyori’s chiral catalyst (Ru–TsDPEN) in methanol solvent. Efficacy of ATH reaction of LA was in...

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Autores principales: Shende, Vaishali S., Raut, Amol B., Raghav, Prathamesh, Kelkar, Ashutosh A., Bhanage, Bhalchandra M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6868911/
https://www.ncbi.nlm.nih.gov/pubmed/31763574
http://dx.doi.org/10.1021/acsomega.9b03424
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author Shende, Vaishali S.
Raut, Amol B.
Raghav, Prathamesh
Kelkar, Ashutosh A.
Bhanage, Bhalchandra M.
author_facet Shende, Vaishali S.
Raut, Amol B.
Raghav, Prathamesh
Kelkar, Ashutosh A.
Bhanage, Bhalchandra M.
author_sort Shende, Vaishali S.
collection PubMed
description [Image: see text] This study presents a first report on ruthenium-catalyzed asymmetric transfer hydrogenation (ATH) of levulinic acid (LA) to chiral γ-valerolactone (GVL). ATH of LA has been explored with Noyori’s chiral catalyst (Ru–TsDPEN) in methanol solvent. Efficacy of ATH reaction of LA was investigated under different reactions conditions such as temperature, catalyst, and hydrogen donor concentration. The effect of various organic tertiary bases along with formic acid (FA) as a hydrogen donor was studied, and N-methylpiperidine with FA (1:1 molar ratio) was revealed as an efficient hydrogen donor for ATH of LA to GVL furnishing chiral GVL with complete conversion and 93% enantiomeric excess (ee). This operationally simple and mild ATH protocol was tested for practical applicability of ATH of LA obtained from biomass waste (rice husk and wheat straw) and furnished chiral GVL with 82% ee.
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spelling pubmed-68689112019-11-22 Room-Temperature Asymmetric Transfer Hydrogenation of Biomass-Derived Levulinic Acid to Optically Pure γ-Valerolactone Using a Ruthenium Catalyst Shende, Vaishali S. Raut, Amol B. Raghav, Prathamesh Kelkar, Ashutosh A. Bhanage, Bhalchandra M. ACS Omega [Image: see text] This study presents a first report on ruthenium-catalyzed asymmetric transfer hydrogenation (ATH) of levulinic acid (LA) to chiral γ-valerolactone (GVL). ATH of LA has been explored with Noyori’s chiral catalyst (Ru–TsDPEN) in methanol solvent. Efficacy of ATH reaction of LA was investigated under different reactions conditions such as temperature, catalyst, and hydrogen donor concentration. The effect of various organic tertiary bases along with formic acid (FA) as a hydrogen donor was studied, and N-methylpiperidine with FA (1:1 molar ratio) was revealed as an efficient hydrogen donor for ATH of LA to GVL furnishing chiral GVL with complete conversion and 93% enantiomeric excess (ee). This operationally simple and mild ATH protocol was tested for practical applicability of ATH of LA obtained from biomass waste (rice husk and wheat straw) and furnished chiral GVL with 82% ee. American Chemical Society 2019-11-05 /pmc/articles/PMC6868911/ /pubmed/31763574 http://dx.doi.org/10.1021/acsomega.9b03424 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Shende, Vaishali S.
Raut, Amol B.
Raghav, Prathamesh
Kelkar, Ashutosh A.
Bhanage, Bhalchandra M.
Room-Temperature Asymmetric Transfer Hydrogenation of Biomass-Derived Levulinic Acid to Optically Pure γ-Valerolactone Using a Ruthenium Catalyst
title Room-Temperature Asymmetric Transfer Hydrogenation of Biomass-Derived Levulinic Acid to Optically Pure γ-Valerolactone Using a Ruthenium Catalyst
title_full Room-Temperature Asymmetric Transfer Hydrogenation of Biomass-Derived Levulinic Acid to Optically Pure γ-Valerolactone Using a Ruthenium Catalyst
title_fullStr Room-Temperature Asymmetric Transfer Hydrogenation of Biomass-Derived Levulinic Acid to Optically Pure γ-Valerolactone Using a Ruthenium Catalyst
title_full_unstemmed Room-Temperature Asymmetric Transfer Hydrogenation of Biomass-Derived Levulinic Acid to Optically Pure γ-Valerolactone Using a Ruthenium Catalyst
title_short Room-Temperature Asymmetric Transfer Hydrogenation of Biomass-Derived Levulinic Acid to Optically Pure γ-Valerolactone Using a Ruthenium Catalyst
title_sort room-temperature asymmetric transfer hydrogenation of biomass-derived levulinic acid to optically pure γ-valerolactone using a ruthenium catalyst
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6868911/
https://www.ncbi.nlm.nih.gov/pubmed/31763574
http://dx.doi.org/10.1021/acsomega.9b03424
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