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dcterms:title
Diastereoselective Addition of Enantiopure Lithiumtert-Butylsulfinylferrocene to Imines
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dcterms:abstract
(S)-tert-Butylsulfinylferrocene was submitted to ortho-metalation, and the corresponding lithium derivativewas trapped by alkyl or aryl imines bearing various electron-withdrawing groups on the nitrogen atom(Ts, Dpp, Boc). New aminosulfoxides were obtained with complete diastereocontrol when Dpp or Bocgroups were used. The absolute configuration (SS,SFc,S) has been determined by single-crystal X-rayanalysis and chemical correlation. An unusual pseudocyclic boatlike transition state has been proposedto explain the stereochemical course of this reaction.
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