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.
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