Photoinduced radical hydroperfluoroalkylation and the synthesis of fluorinated amino acids and peptides

The photoinduced radical hydroperfluoroalkylation of unsaturated carboxylic acids using TTMSS as a H-donor was successfully developed. The stereoselective reaction using Oppolzer's camphorsultum was also achieved to give high stereoselectivity. The reaction was also effective for N-phthalimide-dehydroamino acid and the product was easily converted to the corresponding amino acid and a peptide derivative.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Development of photo-induced radical hydroperfluoroalkylation of olefins including dehydroamino acid, using TTMSS as a H-donor. ► Highly stereoselective reaction via chiral auxiliary method. ► Efficient method for the synthesis of chiral β-perfluoroalkylated amino acids.