Catalytic, Enantioselective 1,2-Difluorination of Cinnamamides

Catalytic, Enantioselective 1,2-Difluorination of Cinnamamides

The enantio- and diastereoselective synthesis of 1,2-difluorides via chiral aryl iodide-catalyzed difluorination of cinnamamides is reported. The method uses HF-pyridine as a fluoride source and mCPBA as a stoichiometric oxidant to turn over catalyst, and affords compounds containing vicinal, fluori...

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Veröffentlicht in:Organic letters 2019-07, Vol.21 (13), p.4919-4923
Hauptverfasser: Haj, Moriana K, Banik, Steven M, Jacobsen, Eric N
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Banik, Steven M
Jacobsen, Eric N
description The enantio- and diastereoselective synthesis of 1,2-difluorides via chiral aryl iodide-catalyzed difluorination of cinnamamides is reported. The method uses HF-pyridine as a fluoride source and mCPBA as a stoichiometric oxidant to turn over catalyst, and affords compounds containing vicinal, fluoride-bearing stereocenters. Selectivity for 1,2-difluorination versus a rearrangement pathway resulting in 1,1-difluorination is enforced through anchimeric assistance from a N-tert-butyl amide substituent.
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title Catalytic, Enantioselective 1,2-Difluorination of Cinnamamides
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