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 language | English |
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Pages (from-to) | 144-152 |
Number of pages | 9 |
Journal | Synthetic Communications |
Volume | 42 |
Issue number | 1 |
DOIs | |
State | Published - Jan 2012 |
ASJC Scopus subject areas
- Organic Chemistry
Keywords
- 4-fluorotryptophan
- Asymmetric synthesis
- fluoroamino acids
- organofluorine chemistry