Enantioselective and diastereoselective synthesis of fluorinated dipeptides by late electrophilic fluorination

Asymmetric synthesis of fluorinated dipeptides by electrophilic fluorination occurs with up to 73:27 enantiomeric ratio and high >98:2 diastereomeric ratio. This constitutes the first example of a direct electrophilic fluorination of dipeptides. A series of optically enriched monofluorinated dipeptides incorporating an α-fluoro-α-amino acid were prepared by enantio- and diastereoselective electrophilic fluorination. This previously unsuccessful approach to fluorinated dipeptides can now be achieved with up to 73:27 enantiomeric ratio and high >98:2 diastereomeric ratio.