A novel class of fluorinated cinchona alkaloids as surface modifiers for the enantioselective heterogeneous hydrogenation of α-ketoesters
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Date
2010-07-15Type
- Journal Article
ETH Bibliography
yes
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Abstract
Novel C-9 fluorinated cinchona alkaloid derivatives were investigated as chiral surface modifiers for the platinum-catalyzed asymmetric heterogeneous hydrogenation of α-ketoesters. Enantioselectivities approaching those observed with the parent alkaloids were obtained, and direct comparison with conformationally labile deoxycinchonidine confirmed that the C-9 fluorine atom is important for performance. In this study, the 9-fluoro derivative of cinchonidine was shown to effect the reduction of ketopantolactone to (R)-pantolactone in quantitative yield with good levels of enantioinduction (57% ee) providing preliminary validation for this novel class of surface modifiers. Show more
Publication status
publishedExternal links
Journal / series
Journal of Molecular Catalysis A: ChemicalVolume
Pages / Article No.
Publisher
ElsevierSubject
Alkaloids; Asymmetric catalysis; Chiral modifier; Fluorine; Gauche effect; HydrogenationOrganisational unit
03285 - Baiker, Alfons (emeritus)
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ETH Bibliography
yes
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