title: Synthesis of alpha-trifluoromethyl alpha-amino acids with aromatic, heteroaromatic and ferrocenyl subunits in the side chain.
abstract: 5-Benzyloxy-4-trifluoromethyl-1,3-oxazoles, obtained from 5-fluoro-4-trifluoromethyloxazoles and benzyl alcohols, are capable for rearrangements. A 1,3 shift of a benzyl group is the key step of a new general route toward alpha-trifluoromethyl substituted aromatic and heteroaromatic amino acids, demonstrating that 5-fluoro-4-trifluoromethyl-1,3-oxazole is a synthetic Tfm-Gly equivalent. On reaction with benzpinacol partially fluorinated oxazoles are transformed into bis(trifluoromethyl) substituted 2,5-diamino adipic acid and N-benzoyl-2-benzhydryl-3,3,3-trifluoroalanine.
authors.affiliation: Department of Organic Chemistry, University of Leipzig, Leipzig, Germany. burger@organik.chemie.uni-leipzig.de
authors.forename: K
authors.initials: K
authors.lastname: Burger
authors.forename: L
authors.initials: L
authors.lastname: Hennig
authors.forename: P
authors.initials: P
authors.lastname: Tsouker
authors.forename: J
authors.initials: J
authors.lastname: Spengler
authors.forename: F
authors.initials: F
authors.lastname: Albericio
authors.forename: B
authors.initials: B
authors.lastname: Koksch
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005296:Ferrous Compounds / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D000075163:Metallocenes; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D005296:Ferrous Compounds; D006841:Hydrocarbons, Aromatic; D006845:Hydrocarbons, Fluorinated; D000075163:Metallocenes; C004998:ferrocene