Synthesis of alpha-trifluoromethyl alpha-amino acids with aromatic, heteroaromatic and ferrocenyl subunits in the side chain.
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.
Burger
K
K
Department of Organic Chemistry, University of Leipzig, Leipzig, Germany. burger@organik.chemie.uni-leipzig.de
Hennig
L
L
Tsouker
P
P
Spengler
J
J
Albericio
F
F
Koksch
B
B
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
D000596:Amino Acids; D005296:Ferrous Compounds; D006841:Hydrocarbons, Aromatic; D006845:Hydrocarbons, Fluorinated; D000075163:Metallocenes; C004998:ferrocene