Beumer, Raphael and Bubert, Christian and Cabrele, Chiara and Vielhauer, Oliver and Pietzsch, Markus and Reiser, Oliver (2000) The synthesis of diastereo- and enantiomerically pure beta-aminocyclopropanecarboxylic acids. JOURNAL OF ORGANIC CHEMISTRY, 65 (26). pp. 8960-8969. ISSN 0022-3263
Full text not available from this repository.Abstract
The synthesis of diastereo- and enantiomerically pure beta -aminocyclopropanecarboxylic acids (beta -ACCs) is described. Starting from pyrrole, (rac)-4 is readily obtained, which was kinetically resolved by enzymatic hydrolysis. Subsequent oxidation of (-)-4 and deformylation gives rise to:the cis-beta -ACC derivative (ent)-9, while (+)-10 was converted to the trans-beta -ACC derivative 8. Both 8 and (ent)-9 and their benzyl esters 13 and is, being conformationally restricted beta -alanine or gamma -aminobutyric acid (GABA) derivatives, represent useful building blocks for peptides containing unnatural amino acids.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PIG-LIVER ESTERASE; OPTICALLY-ACTIVE OXAZOLIDINONES; ENHANCED ANTIOPIATE ACTIVITY; CYCLOPROPANE AMINO-ACIDS; ALGA GRATELOUPIA-CARNOSA; ASYMMETRIC-SYNTHESIS; 1-AMINOCYCLOPROPANECARBOXYLIC ACID; ORGANIC-SYNTHESIS; 1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID; ENANTIOSELECTIVE SYNTHESIS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 08 Mar 2022 10:34 |
| Last Modified: | 08 Mar 2022 10:34 |
| URI: | https://pred.uni-regensburg.de/id/eprint/41968 |
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