Brunner, Henri and Baur, Markus A. (2003) alpha-amino acid derivatives by enantioselective decarboxylation. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (15). pp. 2854-2862. ISSN 1434-193X
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The methodology of enantioselective decarboxylation was applied to 2-aminomalonic acid derivatives in order to obtain enantio-enriched amino acid derivatives. Full conversion was achieved stirring racemic N-acetylated 2-aminomalonic hemiesters in THF at 70 degreesC with 10 mol % of a chiral base for 24 h. The catalyst may be recycled. Whereas the commercially available cinchona alkaloids gave poor results, benzamide and benzenesulfonamide derivatives of 9-amino(9-de-oxy)epicinchonine turned out to be effective catalysts. The best result was obtained with 2-N-acetylamino-2-ethoxycarbonyl-3-phenylpropionic acid as the starting material and N-(9-deoxyepicinchonine-9-yl)-4-methoxybenzdmide as the chiral base to give ethyl N-acetyl-L-phenylalaninate in 70% ee. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CHIRAL COBALT(III) COMPLEXES; INDUCED CASCADE REACTION; ASYMMETRIC-SYNTHESIS; 9-AMINO(9-DEOXY)CINCHONA ALKALOIDS; NAPROXEN DERIVATIVES; BETA-KETOESTERS; MALONIC-ACIDS; CATALYSIS; PROTONATION; COPPER(I); amino acids; asymmetric catalysis; enantioselective decarboxylation; alkaloids; amides |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Henri Brunner |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 05 Aug 2021 05:56 |
| Last Modified: | 05 Aug 2021 05:56 |
| URI: | https://pred.uni-regensburg.de/id/eprint/38811 |
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