Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

• DOI: 10.1021/acs.orglett.0c02465
• Publication Date: 2020-09-21T13:02:06Z
• Authors: Kartic Manna; Hasina Mamataj Begam; Krishanu Samanta; Ranjan Jana
• Keywords: Moiety

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C–H acetoxylation of aryl allyl ether, amine, and amino acids with the retention labile moiety. Mechanistically, reaction proceeds through distinct double-bond isomerization from to vinylic position followed by carboxypalladation β-hydride elimination pathway. For first time, oxidation N-allyl-protected furnish five-membered heterocycles 1,3-syn-addition is established excellent diastereoselectivity.