title: A general and practical palladium-catalyzed monoarylation of β-methyl C(sp³)-H of alanine.
abstract: A palladium-catalyzed monoarylation of β-methyl C(sp(3))-H of an alanine derivative with aryl iodides using an 8-aminoquinoline auxiliary is described. The reaction is highly efficient, scalable and compatible with a variety of functional groups with complete retention of chirality, providing a general and practical access to various β-aryl-α-amino acids. The synthetic potential of this protocol is further demonstrated in the sequential synthesis of diverse β-branched α-amino acids.
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, China. bfshi@zju.edu.cn.
authors.forename: Kai
authors.initials: K
authors.lastname: Chen
authors.forename: Shuo-Qing
authors.initials: SQ
authors.lastname: Zhang
authors.forename: Jing-Wen
authors.initials: JW
authors.lastname: Xu
authors.forename: Fang
authors.initials: F
authors.lastname: Hu
authors.forename: Bing-Feng
authors.initials: BF
authors.lastname: Shi
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D009942:Organometallic Compounds; D010165:Palladium; D000409:Alanine