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Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers

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journal contribution
posted on 2018-04-17, 00:00 authored by Harshkumar H. Patel, Matthew B. Prater, Scott O. Squire, Matthew S. Sigman
This report details a palladium-catalyzed process to access highly functionalized, optically active allylic aryl ethers. A number of electron-deficient alkenyl triflates underwent enantio­selective and site-selective coupling with acyclic aryl enol ethers in the presence of a chiral palladium catalyst. This transform provides chiral allylic ether products in high yields and excellent enantiomeric ratios, furnishing a unique disconnection to incorporate hetero­atoms at a stereo­center. Finally, the applicability of the products to target synthesis was demonstrated through the formation of a chiral allylic alcohol and the generation of a flavone-inspired product.