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Asymmetric fluorination of enamides: access to α-fluoroimines using an anionic chiral phase-transfer catalyst
Robert J Phipps1, Kenichi Hiramatsu, F Dean Toste
1Department of Chemistry, University of California, Berkeley, 94720, United States.
Abstract:
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.
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