title: Stereoselective synthesis of β-alkylated α-amino acids via palladium-catalyzed alkylation of unactivated methylene C(sp3)-H bonds with primary alkyl halides.
abstract: We report a new set of reactions based on the Pd-catalyzed alkylation of methylene C(sp(3))-H bonds of aliphatic quinolyl carboxamides with α-haloacetate and methyl iodide and applications in the stereoselective synthesis of various β-alkylated α-amino acids. These reactions represent the first generally applicable method for the catalytic alkylation of unconstrained and unactivated methylene C-H bonds with high synthetic relevance. When applied with simple isotope-enriched reagents, they also provide a convenient and powerful means to site-selectively incorporate isotopes into the carbon scaffolds of amino acid compounds.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
authors.forename: Shu-Yu
authors.initials: SY
authors.lastname: Zhang
authors.forename: Qiong
authors.initials: Q
authors.lastname: Li
authors.forename: Gang
authors.initials: G
authors.lastname: He
authors.forename: William A
authors.initials: WA
authors.lastname: Nack
authors.forename: Gong
authors.initials: G
authors.lastname: Chen
mesh_terms: D000085:Acetates / Q000737:chemistry; D000478:Alkylation; D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006219:Halogens / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000577:Amides; D000596:Amino Acids; D006219:Halogens; D006847:Hydrocarbons, Iodinated; D010165:Palladium; C014055:methyl iodide