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Rh-catalyzed asymmetric hydrogenation of unsaturated lactate precursors in propylene carbonate.
ChemSusChem. 2008; 1(11):934-40.C

Abstract

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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Publisher Full Text (DOI)

Authors+Show Affiliations

Schäffner B
Leibniz-Institut für Katalyse an der Universität Rostock e.V. Albert-Einstein Strasse 29a, 18059 Rostock, Germany.
Andrushko V
No affiliation info available
Holz J
No affiliation info available
Verevkin SP
No affiliation info available
Börner A
No affiliation info available

MeSH

CatalysisGreen Chemistry TechnologyHydrogenationLactic AcidLigandsPropaneRhodiumSolvents

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18956407

Citation

Schäffner, Benjamin, et al. "Rh-catalyzed Asymmetric Hydrogenation of Unsaturated Lactate Precursors in Propylene Carbonate." ChemSusChem, vol. 1, no. 11, 2008, pp. 934-40.
Schäffner B, Andrushko V, Holz J, et al. Rh-catalyzed asymmetric hydrogenation of unsaturated lactate precursors in propylene carbonate. ChemSusChem. 2008;1(11):934-40.
Schäffner, B., Andrushko, V., Holz, J., Verevkin, S. P., & Börner, A. (2008). Rh-catalyzed asymmetric hydrogenation of unsaturated lactate precursors in propylene carbonate. ChemSusChem, 1(11), 934-40. https://doi.org/10.1002/cssc.200800157
Schäffner B, et al. Rh-catalyzed Asymmetric Hydrogenation of Unsaturated Lactate Precursors in Propylene Carbonate. ChemSusChem. 2008;1(11):934-40. PubMed PMID: 18956407.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rh-catalyzed asymmetric hydrogenation of unsaturated lactate precursors in propylene carbonate. AU - Schäffner,Benjamin, AU - Andrushko,Vasyl, AU - Holz,Jens, AU - Verevkin,Sergey P, AU - Börner,Armin, PY - 2008/10/29/pubmed PY - 2009/2/14/medline PY - 2008/10/29/entrez SP - 934 EP - 40 JF - ChemSusChem JO - ChemSusChem VL - 1 IS - 11 N2 - 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)). SN - 1864-564X UR - https://www.unboundmedicine.com/medline/citation/18956407/Rh_catalyzed_asymmetric_hydrogenation_of_unsaturated_lactate_precursors_in_propylene_carbonate_ L2 - https://doi.org/10.1002/cssc.200800157 DB - PRIME DP - Unbound Medicine ER -