American Chemical Society
ja8b02143_si_001.pdf (42.37 MB)

Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes

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journal contribution
posted on 2018-03-27, 00:00 authored by Katrina M. Mennie, Steven M. Banik, Elaine C. Reichert, Eric N. Jacobsen
The stereoselective synthesis of syn-β-fluoroaziridine building blocks via chiral aryl iodide-catalyzed fluorination of allylic amines is reported. The method employs HF–pyridine as a nucleophilic fluoride source together with mCPBA as a stoichiometric oxidant, and affords access to arylethylamine derivatives featuring fluorine-containing stereocenters in high diastereo- and enantio­selectivity. Catalyst-controlled diastereoselectivity in the fluorination of chiral allylic amines enabled the preparation of highly enantioenriched 1,3-difluoro-2-amines bearing three contiguous stereocenters. The enantioselective catalytic method was applied successfully to other classes of multifunctional alkene substrates to afford anti-β-fluoropyrrolidines, as well as a variety of 1,2-oxyfluorinated products.