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RESEARCH PRODUCT

Organic carbonates as alternative solvents for asymmetric hydrogenation

Jérôme BayardonArmin BörnerVasyl AndrushkoJens HolzBenjamin Schäffner

subject

PharmacologyGreen chemistryChemistryOrganic ChemistryAsymmetric hydrogenationEnantioselective synthesisGreen Chemistry TechnologyStereoisomerismCatalysisSubstrate SpecificityAnalytical Chemistrychemistry.chemical_compoundCarbonic AcidDrug DiscoveryPropylene carbonateSolventsOrganic chemistryRhodiumHydrogenationOrganic ChemicalsSolvent effectsAcetonitrileChirality (chemistry)SpectroscopyPhosphine

description

Organic carbonates like propylene carbonate (PC) or butylene carbonate (BC) belong to the class of aprotic, highly dipolar solvents (AHD). Interestingly, their potential as solvents for asymmetric catalysis has been overlooked for a long time. The aim of this work is to evaluate organic carbonates and other organic solvents like THF, CH2Cl2, and acetonitrile as well as members of the AHD-family (DMF, DMSO, etc.) as media for homogeneous asymmetric hydrogenation. For this reason cationic Rh-complexes based on chiral phosphine ligands were tested in the hydrogenation of typical benchmark substrates. In several trials, significant advantages of organic carbonates were found. In contrast to DMSO, DMF and acetonitrile, in PC and BC high conversion rates and excellent enantioselectivities were usually observed. Chirality 2009. © 2009 Wiley-Liss, Inc.

yearjournalcountryeditionlanguage
2009-10-01Chirality
https://doi.org/10.1002/chir.20720