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(2R)- and (2S)-3-Fluoroalanine and Their N-Methyl Derivatives:  Synthesis and Incorporation in Peptide Scaffolds

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journal contribution
posted on 07.12.2006 by Hamid R. Hoveyda, Jean-François Pinault
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 β-elimination during amide bond formation.