Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective 1,2-Arylfluorination of Internal Enamides

We herein describe a palladium-catalyzed three-component coupling of internal enamides, arylboronic acids, and Selectfluor to access the chiral beta-fluoroaminated moiety with up to 99 % ee. The prefunctionalized oxazolidinone substituted alkene enables the expedient construction of two vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities. The synthetic application is exhibited by selective transformation of the product into various vicinal benzylic fluoride derivatives.

Automated summary

This method efficiently synthesizes the chiral beta-fluoroaminated moiety with high enantioselectivity and exhibits the ability to transform the product into various vicinal benzylic fluoride derivatives with excellent stereo- and enantioselectivities.