title: Asymmetric synthesis of α-aryl amino acids; aryne-mediated diastereoselective arylation.
abstract: An aryne-mediated α-arylation reaction of Schöllkopf's bis-lactim ether is described. Arynes were generated via an ortho-lithiation approach, affording syn-arylated products in up to 94:6 dr with moderate to good yields and excellent regioselectivities. Hydrolysis provided a variety of substituted arylglycines containing a range of functional groups without racemization.
authors.affiliation: Department of Chemistry, Imperial College London, London, UK.
authors.forename: Elizabeth P
authors.initials: EP
authors.lastname: Jones
authors.forename: Peter
authors.initials: P
authors.lastname: Jones
authors.forename: Anthony G M
authors.initials: AG
authors.lastname: Barrett
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001555:Benzene Derivatives; C524146:benzyne