Abstract
The treatment of various N-morpholino amides with TMPZnCl center dot LiCl (TMP= 2,2,6,6-tetramethylpiperidyl) and Mg(OPiv)(2) in THF at 25 degrees C provides solid zinc enolates with enhanced air and moisture stability (t(1/2) in air: 1-3 h) after solvent evaporation. These enolates undergo Pd-and Cucatalyzed cross-couplings with (hetero) aryl bromides as well as allylic and benzylic halides. The arylated N-morpholino amides were converted into various ketones by LaCl3 center dot 2 LiCl mediated acylation with Grignard reagents. The new, solid enolates were used to prepare a potent anti-breast-cancer drug candidate in six steps and 23% overall yield.
| Item Type: | Journal article |
|---|---|
| Faculties: | Chemistry and Pharmacy > Department of Chemistry |
| Subjects: | 500 Science > 540 Chemistry |
| ISSN: | 1433-7851 |
| Language: | English |
| Item ID: | 54349 |
| Date Deposited: | 14. Jun 2018, 09:56 |
| Last Modified: | 04. Nov 2020, 13:34 |
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