75244-26-7Relevant academic research and scientific papers
Stereospezifische 1,2-Wanderungen von Hydroxyl-, Aryl- und Alkylgruppen bei der Nitrosierung von Aminosaeuren in Fluorowasserstoff/pyridin
Keck, Rolf,Retey, Janos
, p. 769 - 772 (1980)
The nitrosation of α-amino acids in hydrogenfluoride/pyridine was reinvestigated.In contrast to recent reports 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.
STEREOSPECIFICITY IN THE TRANSFORMATION OF α-AMINOACIDS INTO FLUOROACIDS
Faustini, Franco,Munari, Sergio De,Panzeri, Achille,Villa, Vittoria,Gandolfi, Carmelo A.
, p. 4533 - 4536 (2007/10/02)
In the reaction of α-aminoacids with excess NaNO2 in polyhydrogen fluoride-pyridine, stereospecific substitution (i.e. retention of configuration) is observed with C6H11CH2CHNH2COOH, while a stereospecific rearrangment occurs in the case of phenylalanine.
