Organic letters

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

HR Hoveyda, JF Pinault

Index: Hoveyda, Hamid R.; Pinault, Jean-Francois Organic Letters, 2006 , vol. 8, # 25 p. 5849 - 5852

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Citation Number: 14

Abstract

A convergent synthetic methodology has been developed to access both (2 S)-and (2 R)-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 ...