1452898-23-5Relevant academic research and scientific papers
A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes
Wu, Jeffrey,Wang, Yi-Ming,Drljevic, Amela,Rauniyar, Vivek,Phipps, Robert J.,Dean Toste
, p. 13729 - 13733 (2013/09/12)
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.
