Development of Photoinduced Perfluoroalkylation and the Synthesis of Fluorinated Amino Acids

Organofluorine compounds have been receiving significant interest in materials science and medicinal chemistry. Addition reactions of perfluoroalkyl iodide to carbon-carbon double bonds are efficient and versatile for the direct introduction of a perfluoroalkyl group onto organic molecules. However studies on the addition of the perfluoroalkyl radical to electron-deficient olefins are scarce, despite the versatility of the products as fluorine-containing building blocks or monomers. Thus, a novel, efficient perfluoroalkylation of electron-deficient olefins is desirable. Recently, we have developed the effective radical hydroxyperfluoroalkylation, iodoperfluoroalkylation and hydroperfluoroalkynation of electron deficient olefins. We report here these new radical perfluoroalkylations of electron deficient olefines and the diastereoselective reactions using chiral auxiliary method. We also describes the synthesis of chiral fluorinated amino acids and peptides based on these reactions.