A new entry to the construction of a quaternary carbon center having a fluorine atom – SN2′ reaction of γ-fluoroallylic alcohol derivatives with various cyanocuprates

Abstract

Treatment of γ-fluoroallylic phosphate with various lower-ordered cyanocuprates derived from Grignard reagents, organolithium, and organozincs gave the corresponding S_N2′ products having a fluorine atom at a quaternary carbon center in excellent yields. This system could be successfully extended to the chiral version, enantiomerically pure fluorine-containing materials also being obtained in high yield.