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?

Organic & Biomolecular Chemistry Pub Date: 2012-08-21 DOI: 10.1039/C2OB25718A

Abstract

Treatment of γ-fluoroallylic phosphate with various lower-ordered cyanocuprates derived from Grignard reagents, organolithium, and organozincs gave the corresponding SN2′ 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.

Graphical abstract: 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
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