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Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions.


ABSTRACT: 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.

SUBMITTER: Annapureddy RR 

PROVIDER: S-EPMC8048691 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions.

Annapureddy Rajasekar Reddy RR   Burg Finn F   Gramüller Johannes J   Golub Tino P TP   Merten Christian C   Huber Stefan M SM   Bach Thorsten T  

Angewandte Chemie (International ed. in English) 20210226 14


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 hig  ...[more]

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