Stereospezifische 1,2-Wanderungen von Hydroxyl-, Aryl- und Alkylgruppen bei der Nitrosierung von Aminosaeuren in Fluorowasserstoff/pyridin

Article abstract of DOI:10.1002/hlca.19800630403

The nitrosation of α-amino acids in hydrogenfluoride/pyridine was reinvestigated.In contrast to recent reports <1> <2> it was found that this reaction takes place either with entire (phenylalanine, tyrosine, threonine) or partial (valine, isoleucine) rearrangement to yield β-fluorocarboxylic acids.Glycine, alanine and α-amino-butanoic acid were converted exclusively into the α-fluorocarboxylic acids.The substitution of the amino group takes place with stereochemical retention as revealed by NMR. examination of the 2-fluoro-3-methylpentanoic acids obtained from L-isoleucine and D-alloisoleucine, respectively.