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Stereospezifische 1,2‐Wanderungen von Hydroxyl‐, Aryl‐ und Alkyl‐ gruppen bei der Nitrosierung von Aminosäuren in Fluorwasserstoff/Pyridin. Vorläufige mitteilung
Author(s) -
Keck Rolf,
Rétey János
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630403
Subject(s) - chemistry , nitrosation , stereochemistry , amino acid , isoleucine , stereospecificity , aryl , phenylalanine , glycine , pyridine , valine , alanine , alkyl , walden inversion , medicinal chemistry , leucine , organic chemistry , biochemistry , catalysis
Stereospecific 1,2‐Migration of Hydroxyl, Aryl and Alkyl Groups during the Nitrosation of Amino Acids in Hydrogenfluoride/Pyridine Vorläufige Mitteilung 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‐aminobutanoic 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.