title: Preparation of α-amino acids by oxidative oxazoline-oxazinone rearrangement-hydrogenation (OOOH). Scope and limitations.
abstract: The range and scope of the oxidative oxazoline-oxazinone rearrangement-hydrogenation sequence (OOOH)--a short, direct asymmetric synthesis of α-amino acids from carboxylic acids--was explored. The highest yet reported diastereoselectivity for hydrogenation of the oxazinone C=N bond (d.r.=>80:1) is disclosed and rationalized with the aid of ab initio molecular calculations.
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Av, Davis, CA 95616, USA.
authors.forename: Chaomin
authors.initials: C
authors.lastname: Liu
authors.forename: Tadeusz F
authors.initials: TF
authors.lastname: Molinski
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D006865:Hydrogenation; D008958:Models, Molecular; D010078:Oxazines / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D010078:Oxazines; D010080:Oxazoles