Maity, Prantik and Koenig, Burkhard (2006) Synthesis of 3-oxo-2,3-dihydropyrrole amino acids as chiral bipeptidomimics. SYNTHESIS-STUTTGART (16). pp. 2719-2724. ISSN 0039-7881,
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We describe the synthesis of a novel chiral dipeptide beta-sheet mimic based on aminomethyl-3-oxo-2,3-diliydropyrrole carboxylic acids. The synthesis uses a palladium-catalyzed allylation with the chiral Trost ligand as a key step for the construction of a quaternary chiral center. This allows the enantioselective conversion of 2-carboxy-3-hydroxy-pyrrole into 3-oxo-2,3-dihydropyrrole-2-allyi-2-carboxylate. The allyl group is subsequently converted into an aldehyde or ester group. Peptide coupling of the 3-oxo-2,3-dihydropyrrole amino acid leads to more extended systems with partially constrained dipeptide units.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ALLYLIC ALKYLATION; DESIGN; DERIVATIVES; MOPAS; pyrroles; 3-oxo-2,3-diliydropyrrole; allylations; amino acids; catalysis; palladium |
| 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: | 03 Feb 2021 11:04 |
| Last Modified: | 03 Feb 2021 11:04 |
| URI: | https://pred.uni-regensburg.de/id/eprint/34163 |
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