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Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes.

ABSTRACT: The stereoselective synthesis of syn-?-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-?-fluoropyrrolidines, as well as a variety of 1,2-oxyfluorinated products.

SUBMITTER: Mennie KM

PROVIDER: S-EPMC5902804 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes.

Mennie Katrina M KM Banik Steven M SM Reichert Elaine C EC Jacobsen Eric N EN

Journal of the American Chemical Society 20180329 14

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 prep ...[more]

PMID: 29583001

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