E. C. Lee, B. L. Hodous, E. Bergin, C. Shih and G. C. Fu, “Catalytic Asymmetric Staudinger Reactions to Form ?-Lactams: An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent,” Journal of the American Chemical Society, Vol. 127, No. 33, 2005, pp. 11586-11587. doi:10.1021/ja052058p

has been cited by the following article:

• TITLE: Investigation of the Role of Electrogenerated N-Heterocyclic Carbene in the Staudinger Synthesis in Ionic Liquid

  AUTHORS: Marta Feroci

  KEYWORDS: Electrosynthesis, NHC, Staudinger Synthesis, ?-Lactams, Organocatalyst, Ionic Liquid

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.1 No.4, December 27, 2011

  ABSTRACT: Electrogenerated N-heterocyclic carbene (NHC), obtained by cathodic reduction of Bmim-BF4, behaves as organocatalyst and base in the Staudinger synthesis from an acyl chloride and a deactivated imine in ionic liquid to yield ?-lactams. The effect of many parameters (temperature, amount of electricity, substituents, presence of an external base) has been evaluated and a tentative mechanism for the Staudinger synthesis in a very polar medium like the ionic liquid reported. The yields of isolated ?-lactams are good, starting from non-electrophilic imines, and predominantly trans lactams are obtained with a good diastereomeric ratio.