Fu, Jiantao and Wurzer, Nikolai and Lehner, Verena and Reiser, Oliver and Davies, Huw M. L. (2019) Rh(II)-Catalyzed Monocyclopropanation of Pyrroles and Its Application to the Synthesis Pharmaceutically Relevant Compounds. ORGANIC LETTERS, 21 (15). pp. 6102-6106. ISSN 1523-7060, 1523-7052
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Here we report Rh(II)-catalyzed monocyclopropanation reactions on pyrroles in the presence of aryldiazoacetates, providing the corresponding dearomatized products with high levels of enantioselectivity (up to >99% ee). Under the catalysis of Rh-2(R-p-PhTPCP)(4), a broad range of pyrrole substrates and aryldiazoacetates are shown to be compatible. Utilizing these valuable chiral building blocks, we further demonstrate the application of this transformation by synthesizing a homo-beta-proline analog and a beta-aminocarboxylic acid (beta-ACC) derivative from the monocyclopropanated product.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | GABA-UPTAKE INHIBITORS; HOMO-BETA-PROLINE; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CATALYZED DECOMPOSITION; ALPHA/BETA-PEPTIDES; ANALOGS; BINDING; ACIDS; VINYLDIAZOMETHANES; |
| 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: | 01 Apr 2020 05:12 |
| Last Modified: | 01 Apr 2020 05:12 |
| URI: | https://pred.uni-regensburg.de/id/eprint/26465 |
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