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 language | English |
|---|---|
| Pages (from-to) | 55-62 |
| Number of pages | 8 |
| Journal | Amino Acids |
| Volume | 31 |
| Issue number | 1 |
| DOIs | |
| State | Published - Jul 2006 |
| Externally published | Yes |
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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