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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 12
BKCSDE 28(12)
December 20, 2007 

Catalytic Enantioselective Fluorination Reactions of α-Cyano Acetates and α-Cyanophosphonates Using Chiral Palladium Complexes
Sun Mi Kim, Young Ku Kang, Min Je Cho, Joo Yang Mang, Dae Young Kim*
Chiral palladium complexes, Electrophilic fluorination, Asymmetric catalysis, α-Cyano acetates, α-Cyanoalkylphosphonates
The catalytic enantioselective electrophilic fluorinations of active methane compounds promoted chiral palladium complexes have been developed. Treatment of α-cyano acetates and α-cyanoalkylphosphonates with N-fluorobenzenesulfonimide as the fluorine source under mild reaction conditions afforded the corresponding α-cyano-α-fluorinated adducts in high yields with excellent enantiomeric excesses (up to 99% ee). These reactions can be conducted in alcoholic solvents without any precaution to exclude water and moisture.
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