Diastereoselective addition of enantiopure lithium tert-butylsulfinylferrocene to imines |
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Authors: | Grach Guillaume Santos Jana Sopkova-de Oliveira Lohier Jean-François Mojovic Ljubica Plé Nelly Turck Alain Reboul Vincent Metzner Patrick |
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Institution: | Laboratoire de Chimie Moléculaire et Thio-organique, UMR CNRS 6507, ENSICAEN, Université de Caen, 14050 Caen, France. |
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Abstract: | (S)-tert-Butylsulfinylferrocene was submitted to ortho-metalation, and the corresponding lithium derivative was 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 Boc groups were used. The absolute configuration (SS,SFc,S) has been determined by single-crystal X-ray analysis and chemical correlation. An unusual pseudocyclic boatlike transition state has been proposed to explain the stereochemical course of this reaction. |
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