Cargando…
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...
Autores principales: | , , , , |
---|---|
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 |
_version_ | 1783472373196914688 |
---|---|
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. |
format | Online Article Text |
id | pubmed-6868911 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT shendevaishalis roomtemperatureasymmetrictransferhydrogenationofbiomassderivedlevulinicacidtoopticallypuregvalerolactoneusingarutheniumcatalyst AT rautamolb roomtemperatureasymmetrictransferhydrogenationofbiomassderivedlevulinicacidtoopticallypuregvalerolactoneusingarutheniumcatalyst AT raghavprathamesh roomtemperatureasymmetrictransferhydrogenationofbiomassderivedlevulinicacidtoopticallypuregvalerolactoneusingarutheniumcatalyst AT kelkarashutosha roomtemperatureasymmetrictransferhydrogenationofbiomassderivedlevulinicacidtoopticallypuregvalerolactoneusingarutheniumcatalyst AT bhanagebhalchandram roomtemperatureasymmetrictransferhydrogenationofbiomassderivedlevulinicacidtoopticallypuregvalerolactoneusingarutheniumcatalyst |