title: The use of chiral lithium amides in the desymmetrisation of N-trialkylsilyl dimethyl sulfoximines.
abstract: BACKGROUND
  Chiral base desymmetrisation of dimethyl sulfoximines could provide a general route to chiral, enantioenriched dialkyl sulfoximines with potential for use in asymmetric catalysis.
  
  
  RESULTS
  Asymmetric deprotonation of N-trialkylsilyl dimethyl sulfoximines with either enantiomer of lithium N,N-bis(1-phenylethyl)amide in the presence of lithium chloride affords enantioenriched sulfoximines on electrophilic trapping. Ketones, ketimines, trialkylsilyl chlorides and activated alkyl halides may be used as electrophiles in the reaction. Furthermore, a modified Horner-Emmons methodology was investigated.
  
  
  CONCLUSIONS
  Simple chiral lithium amides afford products with enantiomeric excesses of up to 70%, illustrating that chiral base desymmetrisation of dimethyl sulfoximines is possible.
authors.affiliation: Institut für Organische Chemie, Landoltweg 1, RWTH Aachen, Aachen 52074, Germany. matthew.mcgrath@oc.rwth-aachen.de
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: McGrath
authors.forename: Carsten
authors.initials: C
authors.lastname: Bolm