Annapureddy, Rajasekar Reddy and Burg, Finn and Gramueller, Johannes and Golub, Tino P. and Merten, Christian and Huber, Stefan M. and Bach, Thorsten (2021) Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 60 (14). pp. 7920-7926. ISSN 1433-7851, 1521-3773
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An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) and a silver-based catalyst system. Key to the success of the reaction is the use of a chiral phenanthroline ligand with a hydrogen bonding site. The enantioselectivity does not depend on the size of the two substituents at the sulfur atom but only on the binding properties of the heterocyclic lactams. A total of 21 chiral sulfimides were obtained in high yields (44-99 %) and with significant enantiomeric excess (70-99 % ee). The sulfimidation proceeds with high site-selectivity and can also be employed for the kinetic resolution of chiral sulfoxides. Mechanistic evidence suggests the intermediacy of a heteroleptic silver complex, in which the silver atom is bound to one molecule of the chiral ligand and one molecule of an achiral 1,10-phenanthroline. Support for the suggested reaction course was obtained by ESI mass spectrometry, DFT calculations, and a Hammett analysis.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ; asymmetric catalysis; enantioselectivity; hydrogen bonds; ligand design; silver |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 20 Sep 2022 06:22 |
| Last Modified: | 20 Sep 2022 06:22 |
| URI: | https://pred.uni-regensburg.de/id/eprint/47592 |
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