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A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes.

ABSTRACT: We report a catalytic enantioselective electrophilic fluorination of alkenes to form tertiary and quaternary C(sp3)-F bonds and generate ?-amino- and ?-aryl-allylic fluorides. The reaction takes advantage of the ability of chiral phosphate anions to serve as solid-liquid phase transfer catalysts and hydrogen bond with directing groups on the substrate. A variety of heterocyclic, carbocyclic, and acyclic alkenes react with good to excellent yields and high enantioselectivities. Further, we demonstrate a one-pot, tandem dihalogenation-cyclization reaction, using the same catalytic system twice in series, with an analogous electrophilic brominating reagent in the second step.


PROVIDER: S-EPMC3752255 | BioStudies | 2013-01-01T00:00:00Z

REPOSITORIES: biostudies

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