Synthesis of (L)-4-fluorotryptophan

David W. Konas, Drilona Seci, Safa Tamimi

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

A new synthesis of stereochemically pure (L)-4-fluorotryptophan [i.e., (2S)-4-fluorotryptophan] in seven steps from 4-fluoroindole is described. A key reaction in the synthetic strategy is a diastereoselective alkylation of the Schollkopf chiral auxiliary with a fluorinated electrophile. All reaction steps are efficient and proceed in at least 80% yield.

Original languageEnglish
Pages (from-to)144-152
Number of pages9
JournalSynthetic Communications
Volume42
Issue number1
DOIs
StatePublished - 1 Jan 2012

Keywords

  • 4-fluorotryptophan
  • Asymmetric synthesis
  • fluoroamino acids
  • organofluorine chemistry

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