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 β-amino- and β-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.

SUBMITTER: Wu J 

PROVIDER: S-EPMC3752255 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature