Grauer, Andreas and Spaeth, Andreas and Ma, Dawei and Koenig, Burkhard (2009) Metal-Catalyzed Derivatization of C-alpha-Tetrasubstituted Amino Acids and Their Use in the Synthesis of Cyclic Peptides. CHEMISTRY-AN ASIAN JOURNAL, 4 (7). pp. 1134-1140. ISSN 1861-4728,
Full text not available from this repository. (Request a copy)Abstract
C-alpha-tetrasubstituted amino acids are important building blocks in the design and preparation of novel peptidomimetics. We report on the functionalization of the C-alpha-tetrasubstituted THF amino acid rac-5 by copper(I) catalyzed N-arylation reactions. The aryl bromide substituent of rac-5 is replaced by a variety of aliphatic and aromatic amines. Intramolecular N-arylation yielded only small amounts of a cyclic tripeptide 2, whereas cyclic tripeptide ethers 4 and 50 were obtained in an enantiomerically pure form from a palladium(0)-catalyzed intramolecular O-arylation.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | O BOND FORMATION; N-ARYLATION; BIOACTIVE PEPTIDES; CONTAINING HETEROCYCLES; COUPLING REACTIONS; HIV-1 PROTEASE; ARYL; TRIPEPTIDE; INHIBITORS; DESIGN; amino acids; cyclization; homogeneous catalysis; peptides; peptidomimetics |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 12 Oct 2020 06:07 |
| Last Modified: | 12 Oct 2020 06:07 |
| URI: | https://pred.uni-regensburg.de/id/eprint/29674 |
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