Direct asymmetric reduction of levulinic acid to gamma-valerolactone: synthesis of a chiral platform molecule

Levulinic acid was directly converted to optically active (S)-gamma-valerolactone, a proposed biomass-based chiral platform molecule. By using a SEGPHOS ligand-modified ruthenium catalyst in methanol as a co-solvent, eventually, 100% chemoselectivity, and 82% enantioselectivity were achieved. The ef...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2015-01, Vol.17 (12), p.5189-5195
Main Authors: Tukacs, Jozsef M, Fridrich, Balint, Dibo, Gabor, Szekely, Edit, Mika, Laszlo T
Format: Article
Language:English
Subjects:
Asymmetry
Catalysts
Composition effects
Conversion
Methyl alcohol
Optical activity
Platforms
Ruthenium
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Summary:Levulinic acid was directly converted to optically active (S)-gamma-valerolactone, a proposed biomass-based chiral platform molecule. By using a SEGPHOS ligand-modified ruthenium catalyst in methanol as a co-solvent, eventually, 100% chemoselectivity, and 82% enantioselectivity were achieved. The effect of the catalyst composition and reaction parameters on the activity and selectivity was investigated in detail. The conversion of a "real" biomass derived levulinic acid to optically active GVL without decreasing the enantioselectivity was also demonstrated.
ISSN:1463-9262
1463-9270
DOI:10.1039/c5gc01099c