title: Catalytic asymmetric synthesis of glutamate analogues.
abstract: Utilizing our lateral metalation coupled with Jacobsen's catalytic asymmetric amino nitrile synthesis, we have demonstrated the ability to synthesize isoxazole-containing amino acid glutamate analogues in high yield and high enantiomeric excesses. Chiral centers alpha or beta at the C-5 position do not detract from diastereoselectivity of the Jacobsen-Strecker reaction. [reaction: see text]
authors.affiliation: Department of Chemistry, University of Idaho, 301 Renfrew Hall, Moscow, ID 83844-2343, USA.
authors.forename: David J
authors.initials: DJ
authors.lastname: Burkhart
authors.forename: Andrew R
authors.initials: AR
authors.lastname: McKenzie
authors.forename: Jared K
authors.initials: JK
authors.lastname: Nelson
authors.forename: Katherine I
authors.initials: KI
authors.lastname: Myers
authors.forename: Xue
authors.initials: X
authors.lastname: Zhao
authors.forename: Kathy R
authors.initials: KR
authors.lastname: Magnusson
authors.forename: Nicholas R
authors.initials: NR
authors.lastname: Natale
mesh_terms: D000818:Animals; D001667:Binding, Competitive; D001921:Brain / Q000378:metabolism; D002384:Catalysis; D005971:Glutamates / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D007555:Isoxazoles / Q000737:chemistry; D051379:Mice; D008956:Models, Chemical; D009474:Neurons / Q000187:drug effects*; D018377:Neurotransmitter Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D005971:Glutamates; D007555:Isoxazoles; D018377:Neurotransmitter Agents