Diastereoselective Addition of Enantiopure Lithium tert-Butylsulfinylferrocene to Imines

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• 作者：Guillaume Grach ; Jana Sopkova-de Oliveira Santos ; Jean-Franç ; ois Lohier ; Ljubica Mojovic ; Nelly Plé ; Alain Turck ; Vincent Reboul ; Patrick Metzner
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：December 22, 2006
• 年：2006
• 卷：71
• 期：26
• 页码：9572 - 9579
• 全文大小：570K
• 年卷期：v.71,no.26(December 22, 2006)
• ISSN：1520-6904

文摘

(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 (S_S,S_Fc,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.