Faderl, Christian and Budde, Simon and Kachkovskyi, Georgiy and Rackl, Daniel and Reiser, Oliver (2018) Visible Light-Mediated Decarboxylation Rearrangement Cascade of omega-Aryl-N-(acyloxy)phthalimides. JOURNAL OF ORGANIC CHEMISTRY, 83 (19). pp. 12192-12206. ISSN 0022-3263,
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A Smiles-type radical rearrangement induced by visible-light-mediated decarboxylation of omega-aryl-N-(acyloxy)phthalimides was developed, giving rise to pharmacologically important substance classes: phenylethylamine derivatives, dihydroisoquinolinones, and benzoazepinones were synthesized on the basis of readily available benzoic acids or benzaldehydes and beta- or gamma-amino acids. This methodology facilitates the synthesis of enantiopure D-amphetamine and of precursors of capsazepinoid bronchodilators.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ELECTRON-TRANSFER MECHANISM; AROMATIC-SUBSTITUTION; CARBOXYLIC-ACIDS; DERIVATIVES; FUNCTIONALIZATION; ACTIVATION; COMPLEXES; CHEMISTRY; ALKENES; |
| 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: | 05 Dec 2019 13:19 |
| Last Modified: | 05 Dec 2019 13:19 |
| URI: | https://pred.uni-regensburg.de/id/eprint/13706 |
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