Please use this identifier to cite or link to this item: http://dx.doi.org/10.18419/opus-6996
Authors: Effenberger, Franz
Kühlwein, Jürgen
Drauz, Karl-Heinz
Title: Darstellung von N-Acyl-2,3-didehydro-2-aminocarbonsäureestern (Aminosäuren ; 16)
Other Titles: Synthesis of N-acyl-2,3-didehydro-2-amino acid esters (Amino acids ; 16)
Issue Date: 1993
metadata.ubs.publikation.typ: Zeitschriftenartikel
metadata.ubs.publikation.source: Justus Liebigs Annalen der Chemie (1993), S. 1295-1301. URL http://dx.doi.org./10.1002/jlac.1993199301211
URI: http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-44543
http://elib.uni-stuttgart.de/handle/11682/7013
http://dx.doi.org/10.18419/opus-6996
Abstract: N-Acyl-2,3-didehydro-2-amino acid esters 3, 5, 7-12, with a great variety of N-substituents, are obtained in good yields by the perrhenate-catalyzed decomposition of methyl 2-azido carboxylates 1 in organic solvents in the presence of the corresponding acyl chlorides 2. By using methyl 2-azidoisovalerate (1a), the conditions (catalyst, solvent, temperature) for the reaction to give 3a were optimized. The reactivity of acyl chlorides can be strongly enhanced with equimolar amounts of dimethyl formamide, which allows a lowering of the decomposition temperature for this reaction. Under these mild reaction conditions also the unstable N-acyldehydroalanine derivative 5f can be obtained in good yield.
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