A Highly stereospecific and efficient synthesis of homopentafluoro- phenylalanine.
A short and efficient synthesis of homopentafluorophenylalanine (6) from oxazolidine aldehyde 1 in 57% overall yield and in > 98% ee is described. The enantiomeric excess of the product was determined by 19F NMR analysis of the coupling product derived from 5 and L-Ser(O-t-Bu)-OCH3, by comparison to a dipeptide obtained from racemic 5.
Department of Chemistry, Tufts University, Medford, Massachusetts 02155, USA.
I Ramesh
IR
Babu
Edward K
EK
Hamill
Krishna
K
Kumar
D002384:Catalysis; D004151:Dipeptides / Q000737:chemistry; D004563:Electrochemistry; D006845:Hydrocarbons, Fluorinated / Q000032:analysis / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014050:Toluene / Q000031:analogs & derivatives / Q000737:chemistry
D004151:Dipeptides; D006845:Hydrocarbons, Fluorinated; D014050:Toluene; D010649:Phenylalanine