Synthesis and reactions of α-fluoro-α-amino amides

Patrick D. Bailey, Andrew N. Boa, Joanne Clayson

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Abstract

N-((S)-1-Phenylethyl)halofluoroethanamides have been investigated as precursors to N-protected a-fluoro-a-amino amides by nucleophilic displacement of halide with nitrogen nucleophiles such as potassium phthalimide, sodium succinimide, sodium glutarimide, trimethylamine and sodium azide. With single diastereoisomers of the iodofluoroethanamide, clean inversion of configuration occurs at room temperature, but subsequent epimerisation may occur as a result of the liberated iodide. The a-fluoro-a-amino amides made underwent a wide variety of reactions depending on conditions, but in many cases the carbon-fluorine bond was compromised. However, reacting trimethylamine and N-((S)-1-phenylethyl)iodofluoroethanamide gave the corresponding a-fluorobetaine amide, and subsequent acidic hydrolysis led to a-fluorobetaine as the first example of an 'unprotected' a-fluoroamino acid. © 2008 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1724-1736
Number of pages13
JournalTetrahedron
Volume65
Issue number8
DOIs
Publication statusPublished - 21 Feb 2009

Keywords

  • Amino acids and derivatives
  • Peptide analogues/mimetics

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    Bailey, P. D., Boa, A. N., & Clayson, J. (2009). Synthesis and reactions of α-fluoro-α-amino amides. Tetrahedron, 65(8), 1724-1736. https://doi.org/10.1016/j.tet.2008.11.061