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Iron-Catalyzed Imidative Kinetic Resolution of Racemic Sulfoxides

Wang, Jun ; Frings, Marcus ; Bolm, Carsten

Chemistry - A European Journal, Jan, 2014, Vol.20(4), p.966(4) [Peer Reviewed Journal]

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  • Title:
    Iron-Catalyzed Imidative Kinetic Resolution of Racemic Sulfoxides
  • Author: Wang, Jun ; Frings, Marcus ; Bolm, Carsten
  • Subjects: Organic Sulfur Compounds ; Iron (Metal) ; Enantiomers ; Alkyl Groups ; Reagents
  • Is Part Of: Chemistry - A European Journal, Jan, 2014, Vol.20(4), p.966(4)
  • Description: Byline: Jun Wang, Marcus Frings, Carsten Bolm Keywords: iron catalysis; kinetic resolution; nitrene transfer; sulfoxides; sulfoximines Abstract Kinetic resolution of racemic sulfoxides requires either custom substrates or shows moderate enantioselectivity, leading to achiral coproducts (such as sulfones) as an intrinsic part of the process. A new strategy is demonstrated that allows the resolution of racemic sulfoxides through catalytic asymmetric nitrene-transfer reactions. This approach gives rise to both optically active sulfoxides and highly enantioenriched sulfoximines. By using a chiral iron catalyst and a readily available iodinane reagent, high selectivity factors have been achieved under very practical reaction conditions. With respect to the substrate scope, it is noteworthy that this unprecedented imidative kinetic resolution of racemic sulfoxides provides access to both aryl-alkyl and dialkyl sulfoximines in highly enantioenriched forms. Author Affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany), Fax: (+49)241-8092391 http://bolm.oc.rwth-aachen.de Current address: School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275 (P.R. China) Supporting information: Additional Supporting Information may be found in the online version of this article As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. CAPTION(S): miscellaneous_information
  • Language: English
  • Identifier: ISSN: 0947-6539

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