A Convenient Method for the Asymmetric Synthesis of Fluorinated α-Amino Acids from Alcohols

Due to their numerous applications, fluorinated amino acids have recently attracted significant attention. The preparation of fluorine-containing phenylalanines, heteroaryl alanines and aliphatic fluorinated amino acids using Mitsunobu-Tsunoda alkylation of a chiral nucleophilic glycine equivalent with readily available alcohol substrates is described. The reaction proceeds in high yields and with excellent diastereoselectivity. This method provides an efficient synthetic route to fluorinated amino acids for which asymmetric approaches are scarce.