Issue 12, 2015

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

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

Supplementary files

Article information

Article type
Paper
Submitted
22 Maijs 2015
Accepted
28 Jūl. 2015
First published
28 Jūl. 2015
This article is Open Access
Creative Commons BY license

Green Chem., 2015,17, 5189-5195

Author version available

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

J. M. Tukacs, B. Fridrich, G. Dibó, E. Székely and L. T. Mika, Green Chem., 2015, 17, 5189 DOI: 10.1039/C5GC01099C

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