Palladium-Catalyzed Stereoretentive Olefination of Unactivated C(sp3)–H Bonds with Vinyl Iodides at Room Temperature: Synthesis of β-Vinyl α-Amino Acids

A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp3)–H bonds of phthaloyl alanine with a broad range of vinyl iodides at room temperature. This reaction represents the first example of the stereoretentive installation of multisubstituted terminal and internal olefins onto unactivated C(sp3)–H bonds. These methods enable access to a wide range of challenging β-vinyl α-amino acid products in a streamlined and controllable fashion, beginning from simple precursors.