Transforming natural amino acids into alpha-alkyl-substituted amino acids with the help of the HOF.CH3CN complex.
Alpha-alkyl amino acids can be efficiently prepared in high yields from the respective amino acids themselves. The key step is the oxidation of the amine function to create the corresponding alpha-nitro acid in a fast and very high yield reaction followed by phase-transfer alkylation and finally reduction to the desired alpha-alkyl amino acid. Several such acids containing aromatic rings or additional carboxylic groups and acids with steric hindrance at the alpha-position are suitable substrates. Several alkyl halides were examined as alkylating agents.
Harel
Tal
T
School of Chemistry, Tel-Aviv University, Tel-Aviv 69978, Israel.
Rozen
Shlomo
S
D000596:Amino Acids / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
D000596:Amino Acids; D003486:Cyanides