Journal
CHEMSUSCHEM
Volume 1, Issue 11, Pages 934-940Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.200800157
Keywords
asymmetric catalysis; homogeneous catalysis; hydrogenation; propylene carbonate; rhodium
Funding
- Graduate School 1213 of the DFG
- INTAS [05-100000-8064]
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The asymmetric hydrogenation of alpha-acetoxy acrylates to O-acetyl lactates with Rh catalysts based on chiral bisphospholane ligands was investigated in propylene carbonate (PC) as green solvent. In contrast to DuPHOS-type ligands, catASium M ligands lead to full conversion of the substrate in PC and induce excellent enantioselectivities for ethyl ester and methyl ester substrates (> 98%). Moreover, the undesired opening of the maleic anhydride moiety of the catASium M ligand observed in MeOH can be prevented under these conditions. The chiral product can be easily separated from the carbonate solvent by distillation in this way, an ecologically benign process for the production of enantiopure lactic acid derivatives was established which offers a highly efficient catalytic transformation in a green solvent under mild conditions (1-10 bar H-2).
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