Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: synthesis of chiral fluorinated amino acids

A novel conjugate hydrofluoroalkylation of alpha,beta-unsaturated acyl-oxazolidinones is described. Using this method, enantiomerically pure beta-trifluoromethylated amino acids were prepared. Trifluorovaline and trifluoroisoleucine were incorporated into peptides and found to show extremely low alpha-helix propensities.