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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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Steiner et al. (2005) studied this question.
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