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

Green Chemistry Pub Date: 2015-07-28 DOI: 10.1039/C5GC01099C

Abstract

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.

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