title: Palladium-catalyzed stereoretentive olefination of unactivated C(sp3)-H bonds with vinyl iodides at room temperature: synthesis of β-vinyl α-amino acids.
abstract: A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp(3))-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(sp(3))-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.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
authors.forename: Bo
authors.initials: B
authors.lastname: Wang
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
authors.forename: Chengxi
authors.initials: C
authors.lastname: Lu
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
authors.forename: Shu-Yu
authors.initials: SY
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
authors.forename: Gang
authors.initials: G
authors.lastname: He
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
authors.forename: William A
authors.initials: WA
authors.lastname: Nack
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
authors.forename: Gong
authors.initials: G
authors.lastname: Chen
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D014753:Vinyl Compounds; C569210:vinyl iodide; D010165:Palladium; D000409:Alanine