Silver‐Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions
نویسندگان
چکیده
An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) silver-based catalyst system. Key to the success reaction is use chiral phenanthroline ligand hydrogen bonding site. The enantioselectivity does not depend on size two substituents at sulfur atom but only binding properties heterocyclic lactams. A total 21 sulfimides were obtained in high yields (44–99 %) significant enantiomeric excess (70–99 % ee). proceeds site-selectivity can also be employed for kinetic resolution sulfoxides. Mechanistic evidence suggests intermediacy heteroleptic silver complex, which bound one molecule an achiral 1,10-phenanthroline. Support suggested course by ESI mass spectrometry, DFT calculations, Hammett analysis.
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ژورنال
عنوان ژورنال: Angewandte Chemie
سال: 2021
ISSN: ['1521-3773', '1433-7851', '0570-0833']
DOI: https://doi.org/10.1002/ange.202016561