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Synthesis of α-trifluoromethyl α-amino acids with aromatic, heteroaromatic and ferrocenyl subunits in the side chain

  • K. Burger
  • , L. Hennig
  • , P. Tsouker
  • , J. Spengler
  • , F. Albericio
  • , B. Koksch
  • Leipzig University
  • Institute for Research in Biomedicine
  • Free University of Berlin

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

5-Benzyloxy-4-trifluoromethyl-1,3-oxazoles, obtained from 5-fluoro-4-trifluoromethyloxazoles and benzyl alcohols, are capable for rearrangements. A 1,3 shift of a benzyl group is the key step of a new general route toward α-trifluoromethyl substituted aromatic and heteroaromatic amino acids, demonstrating that 5-fluoro-4-trifluoromethyl-1,3-oxazole is a synthetic Tfm-Gly equivalent. On reaction with benzpinacol partially fluorinated oxazoles are transformed into bis(trifluoromethyl) substituted 2,5-diamino adipic acid and N-benzoyl-2-benzhydryl-3,3,3-trifluoroalanine.

Original languageEnglish
Pages (from-to)55-62
Number of pages8
JournalAmino Acids
Volume31
Issue number1
DOIs
StatePublished - Jul 2006
Externally publishedYes

Keywords

  • α-Trifluoromethylamino acids
  • 1,3-Benzyl group migration versus Claisen rearrangement
  • 5-Fluoro-4-trifluoromethyl-1,3-oxazoles
  • Nucleophilic heteroaromatic substitution
  • Synthetic Tfm-Gly equivalent

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