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A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes.
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ABSTRACT:
SUBMITTER: Wu J
PROVIDER: S-EPMC3752255 | biostudies-literature | 2013 Aug
REPOSITORIES: biostudies-literature
Publications
A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes.
Proceedings of the National Academy of Sciences of the United States of America 20130806 34
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 demons ...[more]