ja8b02143_si_001.pdf (42.37 MB)
Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes
journal contributionposted 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.
allylic aminesdifluorodiastereoselectivityvarietystereoselective synthesisenantioenrichedHF-2-aminepreparationAlkeneCatalyst-controlledfluorine-containing stereocentersEnantioselective Fluoroaminationenantioaccessm CPBAmethodsyn -β- fluoroaziridine building blockschiral allylic aminesoxyfluorinatedchiral aryl iodide-catalyzed fluorinationmultifunctional alkene substrates-β- fluoropyrrolidinesstoichiometric oxidantnucleophilic fluoride sourcearylethylamine derivativesCatalytic Diastereoenantioselectivediastereo