Please use this identifier to cite or link to this item: http://dx.doi.org/10.18419/opus-1112
Authors: Effenberger, Franz
Zoller, Gerhard
Title: Investigations on the synthesis of DL-serine from α-haloacrylic acid derivatives (Aminoacids ; 13)
Issue Date: 1988
metadata.ubs.publikation.typ: Zeitschriftenartikel
metadata.ubs.publikation.source: Tetrahedron 44 (1988), S. 5573-5582. URL http://dx.doi.org./10.1016/S0040-4020(01)86062-2
URI: http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-43550
http://elib.uni-stuttgart.de/handle/11682/1129
http://dx.doi.org/10.18419/opus-1112
Abstract: The alkoxide-catalyzed addition of alcohols to α-chloroacrylonitrile at -35°C gives rise to 3-alkoxy-2-chloropropanenitriles; at 0–5°C with excess alkyl 3-alkoxy-2-chloropropanimidates are obtained. The yields of 3 or 4 decrease with increasing pKa values of the alcohols. In the base-catalyzed addition of phenols 5 to 1, a temperature-dependent addition equilibrium is set up in which the position of equilibrium is shifted in favour of the addition products with increasing pKa values of 5. The 3-alkoxy-2-chloropropanoates, which are readily accessible by hydrolysis of 4, react smoothly with sodium azide in the presence of a phase transfer catalyst to furnish the 3-alkoxy-2-azidopropanoates. Starting from benzyl 2-azido-3-benzyloxy-propanoate (10b), the specific syntheses of DL-serine (14), DL-serine hydrochloride (14·HCl), DL-serine methyl ester hydrochloride (13a·HCl), 0-benzyl-DL-serine (12b), and 0-benzyl-DL-serine benzyl ester hydrochloride (11b·HCl) are possible by variation of the hydrogenation conditions.
Appears in Collections:03 Fakultät Chemie

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