Pilsl, Ludwig K. A. and Ertl, Thomas and Reiser, Oliver (2017) Enantioselective Three-Step Synthesis of Homo-beta-proline: A Donor-Acceptor Cyclopropane as Key Intermediate. ORGANIC LETTERS, 19 (10). pp. 2754-2757. ISSN 1523-7060, 1523-7052
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An enantioselective three-step synthesis of the GABA uptake inhibitor (S)-(+)-homo-beta-proline was developed. The basis for the synthesis was the enantioselective Cu-I-catalyzed cyclopropanation of N-Boc-pyrrole, a substrate that persistently has proved to be challenging in such transformations. The cyclopropanation can be performed on a 150 mmol scale, and the two subsequent steps (i.e., hydrogenation and in situ cyclopropane-opening/double-deprotection) toward the target molecule proceed smoothly in quantitative yield without loss of enantiopurity.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | GABA-UPTAKE INHIBITORS; AMINOCYCLOPROPANE CARBOXYLIC-ACIDS; ASYMMETRIC CYCLOPROPANATION; ALPHA/BETA-PEPTIDES; CHIRAL LIGANDS; AMINO-ACIDS; ANALOGS; BINDING; PYRROLIDIN-2-ONES; CONFORMATIONS; |
| 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: | 14 Dec 2018 13:10 |
| Last Modified: | 19 Feb 2019 15:28 |
| URI: | https://pred.uni-regensburg.de/id/eprint/871 |
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