Asymmetric fluorination of enamides: Access to α-fluoroimines using an anionic chiral phase-transfer catalyst
The use of a BINOL-derived phosphate as a chiral anionic phase-transfer catalyst in a nonpolar solvent allows the enantioselective fluorination of enamides using Selectfluor as the fluorinating reagent. We demonstrate that a wide range of stable and synthetically versatile α-(fluoro)benzoylimines can be readily accessed with high enantioselectivity. These compounds have the potential to be readily elaborated into a range of highly stereodefined β-fluoroamines, compounds that constitute highly valuable building blocks of particular importance in the synthesis of pharmaceuticals.
Phipps, Robert J.,Hiramatsu, Kenichi,Toste, F. Dean
p. 8376 - 8379
(2012/06/30)
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