Synthesis of (L)-4-fluorotryptophan

David Konas, Drilona Seci, Safa Tamimi

Research output: Contribution to journalArticle

6 Citations (Scopus)

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

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Alkylation
4-fluorotryptophan

Keywords

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

Cite this

Konas, David ; Seci, Drilona ; Tamimi, Safa. / Synthesis of (L)-4-fluorotryptophan. In: Synthetic Communications. 2012 ; Vol. 42, No. 1. pp. 144-152.
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Synthesis of (L)-4-fluorotryptophan. / Konas, David; Seci, Drilona; Tamimi, Safa.

In: Synthetic Communications, Vol. 42, No. 1, 01.01.2012, p. 144-152.

Research output: Contribution to journalArticle

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AU - Konas, David

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AU - Tamimi, Safa

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AB - 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.

KW - 4-fluorotryptophan

KW - Asymmetric synthesis

KW - fluoroamino acids

KW - organofluorine chemistry

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