Angewandte Chemie International Edition · 2005 · 328 citations · 47 references
Natural SciencesChemistryCatalysisOrganic ChemistryDiversity-oriented SynthesisOrganic AcidsOrganic SynthesisAldehydesAsymmetric CatalysisAsymmetric SynthesisEnantioselective SynthesisFluorine ChemistryOrganocatalysis
Linear and branched aldehydes are asymmetrically α-fluorinated with L-proline- and pyrrolidine-based organocatalysts (see scheme; NFSi: N-fluorobenzenesulfonamide). In the first case, yields and enantioselectivities were high; in the second, the yields remained high and the enantioselectivities were moderate. Significantly, linear aldehydes were only monofluorinated.
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