(2R)- and (2S)-3-fluoroalanine and their N-methyl derivatives:: Synthesis and incorporation in peptide scaffolds

[GRAPHICS] A convergent synthetic methodology has been developed to access both (2S)- and (2R)-3-fluoroalanine and their corresponding N-methyl analogues, in optically pure form, through a common oxazolidinone intermediate that can be obtained from L- or D-serine. In addition, a procedure for incorporation of these unnatural amino acids in peptide scaffolds is also disclosed herein that minimizes the occurrence of,- elimination during amide bond formation.