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

Vaishali S. Shende | Zendy; Amol B. Raut | Zendy; Prathamesh Raghav | Zendy; Ashutosh A. Kelkar | Zendy; Bhalchandra M. Bhanage | Zendy

Open Access

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

Author(s) -

Vaishali S. Shende,

Amol B. Raut,

Prathamesh Raghav,

Ashutosh A. Kelkar,

Bhalchandra M. Bhanage

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.9b03424

Subject(s) - levulinic acid , ruthenium , catalysis , biomass (ecology) , transfer hydrogenation , chemistry , materials science , chemical engineering , organic chemistry , photochemistry , oceanography , engineering , geology

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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