Journal
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
Volume 110, Issue 34, Pages 13729-13733Publisher
NATL ACAD SCIENCES
DOI: 10.1073/pnas.1304346110
Keywords
asymmetric; organocatalysis; hydrogen-bonding
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Funding
- University of California
- Amgen
- European Commission
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM104534] Funding Source: NIH RePORTER
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We report a catalytic enantioselective electrophilic fluorination of alkenes to form tertiary and quaternary C(sp3)-F bonds and generate beta-amino- and beta-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.
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