New and effective routes to fluoro analogs of aliphatic and aromatic amino acids

1-Azaallylic Anions in Heterocyclic Chemistry

“…118 The synthesis of indolizidine 403 (δ-coniceine) could be achieved by regioselective deprotonation of 6-methyl-2,3,4,5-tetrahydropyridine (400) at -78°C and subsequent reaction with 174 (Scheme 73). 119 Reaction at higher temperature resulted in increasing N-alkylation.…”

Nucleophilic addition of 3,3,3-trifluoropropynyllithium to d-glyceraldimine: Concise synthesis of both enantiomers of 5,5,5-trifluoronorvaline

“…In addition, Bocprotected (S)-5,5,5-trifluorovaline 7b was also obtained in 67% yield over two steps from 5b using the same procedure. [20]. Therefore, the absolute configuration of Bocprotected (S)-5,5,5-trifluorovaline 7b was confirmed.…”

“…Therefore, several synthetic routes to 5,5,5-trifluoronorvaline were developed. In most cases racemic mixtures of 5,5,5-trifluoronorvaline were obtained [14][15][16][17][18][19][20]. To the best of our knowledge, there was only one report about the stereoselective synthesis of 5,5,5-trifluoronorvaline, in which the fluorinated reagent SF 4 was used [19].…”

Novel trifluoromethyl-containing peptides as inhibitors for angiotensin-converting enzyme and enkephalin-aminopeptidase

“…Incorporation of both TFM and an indoline residue unexpectedly gives a less potent captopril analog, 2-(R,S). Enalaprilat analogs derived from replacement of the alanine residue, with (S)-TFM-norvaline (L-TFNV) [5], 3-(SS,S), and (S)-TFM-norleucine (t.-TFNL) [5] residues, 4-(S,S,S), gave moderately potent peptides. The other diastereomers of 2-4 exhibited 2-5 order of magnitude weaker activities as predicted.…”