A Highly stereospecific and efficient synthesis of homopentafluoro- phenylalanine

J Org Chem. 2004 Aug 6;69(16):5468-70. doi: 10.1021/jo049206z.

Abstract

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.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Catalysis
  • Dipeptides / chemistry
  • Electrochemistry
  • Hydrocarbons, Fluorinated / analysis
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / analysis
  • Phenylalanine / chemical synthesis*
  • Stereoisomerism
  • Toluene / analogs & derivatives
  • Toluene / chemistry

Substances

  • Dipeptides
  • Hydrocarbons, Fluorinated
  • Toluene
  • Phenylalanine