Rasappan, Ramesh and Olbrich, Tobias and Reiser, Oliver (2009) Combining Fluorous and Triazole Moieties for the Tagging of Chiral Azabis(oxazoline) Ligands. ADVANCED SYNTHESIS & CATALYSIS, 351 (11-12). pp. 1961-1967. ISSN 1615-4150, 1615-4169
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New fluorous-tagged azabis(oxazoline) ligands were prepared using the copper-catalyzed azide-alkyne cycloaddition as ligation method. The resulting ligands were tested in copper-catalyzed asymmetric benzoylations (up to 99% ee), nitroaldol (up to 90% ee), and Michael reactions (up to 82% ee). The combination of unpolar fluorinated alkyl chains and polar triazole moieties imposes properties that are beneficial for the catalysts with respect to recyclability and selectivity. The scope and limitation of this strategy in comparison to analogous catalysts immobilized on methoxypolyethylene glycol (MeOPEG) or polystyrene is discussed. Moreover, this study shows that the choice of solvent for a given reaction is crucial to arrive at highly recyclable bis(oxazoline) catalysts.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CATALYZED ASYMMETRIC REACTIONS; BIS(OXAZOLINE) LIGANDS; BIPHASIC CATALYSIS; MICHAEL ADDITION; RECYCLABLE ORGANOCATALYST; ALDOL REACTION; COMPLEXES; CYCLOPROPANATION; PERFLUOROALKYL; OLEFINS; azabis(oxazolines); click reaction; fluorous tags; immobilization; kinetic resolution; nitroaldol reaction |
| 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: | 09 Sep 2020 09:55 |
| Last Modified: | 09 Sep 2020 09:55 |
| URI: | https://pred.uni-regensburg.de/id/eprint/28576 |
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